Organic light-emitting device, composition for organic layer of organic lightemitting device, and method for manufacturing organic light-emitting device

ABSTRACT

The present specification relates to an organic light emitting device comprising a first electrode, a second electrode, and an organic material layer comprising one or more layers provided between the first electrode and the second electrode, wherein the one or more layers of the organic material layer comprise a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2, a composition for the organic material layer of the organic light emitting device, and a method for manufacturing the organic light emitting device.

TECHNICAL FIELD

This application claims priority to and the benefits of Korean PatentApplication No. 10-2020-0125761, filed with the Korean IntellectualProperty Office on Sep. 28, 2020, the entire contents of which areincorporated herein by reference.

The present specification relates to an organic light emitting device, acomposition for an organic material layer of the organic light emittingdevice, and a method for manufacturing the organic light emittingdevice.

BACKGROUND ART

An organic electroluminescent device is a kind of self-emission typedisplay device, and has advantages of a wide viewing angle, excellentcontrast, and fast response speed.

The organic light emitting device has a structure in which an organicthin film is disposed between two electrodes. When a voltage is appliedto the organic light emitting device having such a structure, light isemitted while they are disappeared after electrons and holes injectedfrom the two electrodes combine in the organic thin film to form a pair.The organic thin film may be composed of a single layer or multiplelayers as needed.

A material of the organic thin film may have a light emitting functionas needed. For example, as the material of the organic thin film, acompound capable of forming a light emitting layer for itself may beused, or a compound capable of serving as a host or dopant of ahost-dopant based light emitting layer may also be used. Besides that, acompound capable of performing the roles of hole injection, holetransport, electron blocking, hole blocking, electron transport,electron injection, and the like may also be used as the material of theorganic thin film.

In order to improve the performance, lifespan, or efficiency of theorganic light emitting device, the development of the material of theorganic thin film is continuously required.

PRIOR ART DOCUMENTS Patent Documents

-   U.S. Pat. No. 4,356,429

DISCLOSURE Technical Problem

The present disclosure is directed to providing an organic lightemitting device comprising a compound having a chemical structure whichcan satisfy conditions required for materials usable in the organiclight emitting device, such as an appropriate energy level,electrochemical stability, thermal stability, etc., and can play variousroles required in the organic light emitting device depending onsubstituents, a composition for an organic material layer of the organiclight emitting device, and a method for manufacturing the organic lightemitting device.

Technical Solution

An embodiment of the present application provides an organic lightemitting device comprising a first electrode, a second electrode, and anorganic material layer comprising one or more layers provided betweenthe first electrode and the second electrode, wherein the one or morelayers of the organic material layer comprise a heterocyclic compoundrepresented by Chemical Formula 1 below and a heterocyclic compoundrepresented by Chemical Formula 2 below.

In Chemical Formulas 1 and 2 above,

X is O; or S,

R1 to R8, and Rc and Rd are the same as or different from each other,and are each independently selected from the group comprising hydrogen;deuterium; a halogen; a cyano group; a substituted or unsubstitutedC1-C60 alkyl group; a substituted or unsubstituted C2-C60 alkenyl group;a substituted or unsubstituted C2-C60 alkynyl group; a substituted orunsubstituted C1-C60 alkoxy group; a substituted or unsubstituted C3-C60cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkylgroup; a substituted or unsubstituted C6-C60 aryl group; a substitutedor unsubstituted C2-C60 heteroaryl group; —SiRR′R″; —P(═O)RR′; and—NRR′, or two or more groups adjacent to each other are bonded to eachother to form a substituted or unsubstituted aromatic hydrocarbon ringor a substituted or unsubstituted heterocycle ring,

X1 to X3 are N; or CRe, and at least one of X1 to X3 is N,

L1 and L2 are the same as or different from each other and are eachindependently a direct bond; a substituted or unsubstituted C6-C60arylene group; or a substituted or unsubstituted C2-C60 heteroarylenegroup,

Ar1 and Ar2 are the same as or different from each other and are eachindependently a substituted or unsubstituted C1-C60 alkyl group; asubstituted or unsubstituted C6-C60 aryl group; or a substituted orunsubstituted C2-C60 heteroaryl group,

Ra and Rb are the same as or different from each other and are eachindependently —CN; —SiRR′R″; a substituted or unsubstituted C6-C60 arylgroup; or a substituted or unsubstituted C2-C60 heteroaryl group,

R, R′, R″, and Re are the same as or different from each other and areeach independently hydrogen; deuterium; a substituted or unsubstitutedC1-C60 alkyl group; or a substituted or unsubstituted C6-C60 aryl group,

n, p, and a are an integer of 0 to 4,

r and s are an integer of 0 to 7,

q is an integer of 1 to 5, and

when n, p, a, s, q, and r are 2 or more, the substituents in parenthesesare the same as or different from each other.

Further, another embodiment of the present application provides acomposition for an organic material layer of the organic light emittingdevice, comprising the heterocyclic compound represented by ChemicalFormula 1 above and the heterocyclic compound represented by ChemicalFormula 2 above.

Finally, an embodiment of the present application provides a method formanufacturing the organic light emitting device, comprising the stepsof: preparing a substrate; forming a first electrode on the substrate;forming an organic material layer comprising one or more layers on thefirst electrode; and forming a second electrode on the organic materiallayers, wherein the step of forming the organic material layerscomprises a step of forming an organic material layer comprising one ormore layers using a composition for the organic material layer accordingto the present application.

Advantageous Effects

The heterocyclic compound according to an embodiment of the presentapplication may be used as an organic material layer material of anorganic light emitting device. The heterocyclic compound may be used asa material for a hole injection layer, a hole transport layer, a lightemitting layer, an electron transport layer, an electron injectionlayer, a charge generation layer, etc. in the organic light emittingdevice. In particular, the heterocyclic compound represented by ChemicalFormula 1 above and the heterocyclic compound represented by ChemicalFormula 2 above may be simultaneously used as a material of the lightemitting layer of the organic light emitting device. Further, when theheterocyclic compound represented by Chemical Formula 1 above and theheterocyclic compound represented by Chemical Formula 2 above aresimultaneously used in the organic light emitting device, drivingvoltage of the device may be lowered, light efficiency may be improved,and thermal stability of the compounds may cause lifespancharacteristics of the device to be improved.

In particular, the heterocyclic compound represented by Chemical Formula1 above has a linking group of a phenylene group in the core structureof dibenzofuran or dibenzothiophene, and has a substituent of azines.Accordingly, it may have characteristics of enabling the driving voltageto be reduced and enabling the efficiency and lifespan to be maximizedby enhancing characteristics of the n-type and comprising a heterocycliccompound together corresponding to biscarbazoles having a specificsubstituent represented by Chemical Formula 2 above.

Specifically, in the heterocyclic compound of Chemical Formula 1 above,HOMO is localized in dibenzofuran and dibenzothiophene to effectivelystabilize holes, and LUMO is localized in an azine-based substituent toeffectively stabilize electrons. Therefore, it is especially effectivewhen used as a host of the light emitting layer.

DESCRIPTION OF DRAWINGS

FIGS. 1 to 3 are diagrams each schematically illustrating a laminationstructure of an organic light emitting device according to an embodimentof the present application.

MODE FOR DISCLOSURE

Hereinafter, the present application will be described in detail.

The term “substitution” means that a hydrogen atom bonded to a carbonatom of a compound is replaced with another substituent, and theposition to be substituted is not limited as long as it is a position atwhich the hydrogen atom is substituted, that is, a position where thesubstituent is substitutable, and when two or more are substituted, twoor more substituents may be the same as or different from each other.

In the present specification, “substituted or unsubstituted” means thatit is substituted or unsubstituted with one or more substituentsselected from the group comprising deuterium; a cyano group; a halogengroup; an C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynylgroup; a C3-C60 cycloalkyl group; a C2-C60 heterocycloalkyl group; aC6-C60 aryl group; a C2-C60 heteroaryl group; a silyl group; a phosphineoxide group; and an amine group, or is substituted or unsubstituted witha substituent to which two or more substituents selected from theabove-exemplified substituents are connected.

In the present specification, “when a substituent is not indicated in aChemical Formula or compound structure” means that a hydrogen atom isbonded to a carbon atom. However, since deuterium (²H) is an isotope ofhydrogen, some hydrogen atoms may be deuterium.

In an embodiment of the present application, “when a substituent is notindicated in a Chemical Formula or compound structure” may mean that allpositions where a substituent can come are hydrogen or deuterium. Thatis, deuterium may be an isotope of hydrogen, and some hydrogen atoms maybe deuterium that is an isotope, and the content of deuterium may be 0to 100% at this time.

In an embodiment of the present application, in the case of “when asubstituent is not indicated in a Chemical Formula or compoundstructure”, if deuterium is not explicitly excluded, such as the contentof deuterium of 0%, the content of hydrogen of 100%, etc., hydrogen anddeuterium may be mixed and used in the compound. That is, whenexpressing “substituent X is hydrogen”, deuterium is not excluded, suchas the content of hydrogen of 100%, the content of deuterium of 0%,etc., it may mean a state in which hydrogen and deuterium are mixed.

In an embodiment of the present application, deuterium is an elementhaving a deuteron comprising one proton and one neutron as one of theisotopes of hydrogen as a nucleus, it may be expressed as hydrogen-2,and an element symbol may also be written as D or 2H.

In an embodiment of the present application, although isotopes meaningatoms which have the same atomic number (Z), but have different massnumbers (A) have the same number of protons, they may also beinterpreted as elements with different numbers of neutrons.

In an embodiment of the present application, when the total number ofsubstituents that a basic compound may have is defined as T1, and thenumber of the specific substituents among them is defined as T2, themeaning of the content T % of specific substituents may be defined asT2/T1×100=T %.

That is, as an example, the 20% content of deuterium in the phenyl grouprepresented by

may be expressed as 20% when the total number of substituents that thephenyl group may have is 5 (T1 in the formula) and the number ofdeuteriums among them is 1 (T2 in the formula). That is, it may berepresented by the structural formula below that the content ofdeuterium in the phenyl group is 20%.

Further, in an embodiment of the present application, “a phenyl grouphaving a deuterium content of 0%” may mean a phenyl group that does notcontain a deuterium atom, that is, has 5 hydrogen atoms.

In the present specification, the halogen may be fluorine, chlorine,bromine, or iodine.

In the present specification, the alkyl group comprises a linear orbranched chain having 1 to 60 carbon atoms, and may be furthersubstituted by other substituents. The number of carbon atoms of thealkyl group may be 1 to 60, specifically 1 to 40, and more specifically1 to 20. Specific examples of the alkyl group may comprise a methylgroup, an ethyl group, a propyl group, an n-propyl group, an isopropylgroup, a butyl group, an n-butyl group, an isobutyl group, a tert-butylgroup, a sec-butyl group, a 1-methyl-butyl group, an 1-ethyl-butylgroup, a pentyl group, an n-pentyl group, an isopentyl group, aneopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group,an 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentylgroup, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group,an n-heptyl group, an 1-methylhexyl group, a cyclopentylmethyl group, acyclohexylmethyl group, an octyl group, an n-octyl group, a tert-octylgroup, an 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentylgroup, an n-nonyl group, a 2,2-dimethylheptyl group, an 1-ethyl-propylgroup, an 1,1-dimethyl-propyl group, an isohexyl group, a 2-methylpentylgroup, a 4-methylhexyl group, a 5-methylhexyl group, etc., but are notlimited thereto.

In the present specification, the alkenyl group may comprise a linear orbranched chain having 2 to 60 carbon atoms, and may be furthersubstituted by other substituents. The number of carbon atoms of thealkenyl group may be 2 to 60, specifically 2 to 40, and morespecifically 2 to 20. Specific examples of the alkenyl group maycomprise a vinyl group, an 1-propenyl group, an isopropenyl group, an1-butenyl group, a 2-butenyl group, a 3-butenyl group, an 1-pentenylgroup, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenylgroup, an 1,3-butadienyl group, an allyl group, an 1-phenylvinyl-1-ylgroup, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stylbenyl group, a styrenylgroup, etc., but are not limited thereto.

In the present specification, the alkynyl group may comprise a linear orbranched chain having 2 to 60 carbon atoms, and may be furthersubstituted by other substituents. The number of carbon atoms of thealkynyl group may be 2 to 60, specifically 2 to 40, and morespecifically 2 to 20.

In the present specification, the alkoxy group may be a linear,branched, or cyclic chain. The number of carbon atoms of the alkoxygroup is not particularly limited, but is preferably 1 to 20. Specificexamples of the alkoxy group may comprise methoxy, ethoxy, n-propoxy,isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy,n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy,3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy,n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limitedthereto.

In the present specification, the cycloalkyl group may comprise amonocyclic or polycyclic ring having 3 to 60 carbon atoms, and may befurther substituted by other substituents. Here, the polycyclic ringrefers to a group in which a cycloalkyl group is directly connected orcondensed with other ring group. Here, although the other ring group maybe a cycloalkyl group, it may also be a different type of ring group,for example, a heterocycloalkyl group, an aryl group, a heteroarylgroup, or the like. The number of carbon atoms of the cycloalkyl groupmay be 3 to 60, specifically 3 to 40, and more specifically 5 to 20.Specific examples of the cycloalkyl group may comprise a cyclopropylgroup, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentylgroup, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a3-methylcyclohexyl group, a 4-methylcyclohexyl group, a2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group,etc., but are not limited thereto.

In the present specification, the heterocycloalkyl group may comprise O,S, Se, N, or Si as a heteroatom, may comprise a monocyclic or polycyclicring having 2 to 60 carbon atoms, and may be further substituted byother substituents. Here, the polycyclic ring refers to a group in whicha heterocycloalkyl group is directly connected or condensed with otherring group. Here, although the other ring group may be aheterocycloalkyl group, it may also be a different type of ring group,for example, a cycloalkyl group, an aryl group, a heteroaryl group, orthe like. The number of carbon atoms of the heterocycloalkyl group maybe 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

In the present specification, the aryl group may comprise a monocyclicor polycyclic ring having 6 to 60 carbon atoms, and may be furthersubstituted by other substituents. Here, the polycyclic ring means agroup in which an aryl group is directly connected or condensed withother ring group. Here, although the other ring group may be an arylgroup, it may also be a different type of ring group, for example, acycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or thelike. The aryl group comprises a spiro group. The number of carbon atomsof the aryl group may be 6 to 60, specifically 6 to 40, and morespecifically 6 to 25. Specific examples of the aryl group may comprise aphenyl group, a biphenyl group, a triphenyl group, a naphthyl group, ananthryl group, a chrysenyl group, a phenanthrenyl group, a perylenylgroup, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group,a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenylgroup, an indenyl group, an acenaphthylenyl group, a benzofluorenylgroup, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group,condensed ring groups thereof, etc., but are not limited thereto.

In the present specification, the fluorenyl group may be substituted,and adjacent substituents may be bonded to each other to form a ring.

When the fluorenyl group is substituted, it may become

etc., but is not limited thereto.

In the present specification, the heteroaryl group may comprise S, O,Se, N, or Si as a heteroatom, may comprise a monocyclic or polycyclicring having 2 to 60 carbon atoms, and may be further substituted byother substituents. Here, the polycyclic ring refers to a group in whicha heteroaryl group is directly connected or condensed with other ringgroup. Here, although the other ring group may be a heteroaryl group, itmay also be a different type of ring group, for example, a cycloalkylgroup, a heterocycloalkyl group, an aryl group, or the like. The numberof carbon atoms of the heteroaryl group may be 2 to 60, specifically 2to 40, and more specifically 3 to 25. Specific examples of theheteroaryl group may comprise a pyridyl group, a pyrrolyl group, apyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenegroup, an imidazolyl group, a pyrazolyl group, an oxazolyl group, anisoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolylgroup, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, adithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranylgroup, a diazinyl group, an oxazinyl group, a thiazinyl group, adeoxynyl group, a triazinyl group, a tetrazinyl group, a quinolyl group,an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, aquinozolilyl group, a naphthyridyl group, an acridinyl group, aphenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenylgroup, a triazaindene group, an indolyl group, an indolizinyl group, abenzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, abenzothiophene group, a benzofuran group, a dibenzothiophene group, adibenzofuran group, a carbazolyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a phenazinyl group, a dibenzosilol group, aspirobi (dibenzosilol) group, dihydrophenazinyl group, a phenoxazinylgroup, a phenantridyl group, an imidazopyridinyl group, a thienyl group,an indolo[2,3-a]carbazolyl group, an indolo[2,3-b]carbazolyl group, anindolinyl group, a 10,11-dihydro-dibenzo[b,f]azepine group, a9,10-dihydroacridinyl group, a phenanthrazinyl group, a phenothiazinylgroup, a phthalazinyl group, a naphthylidinyl group, a phenanthrolinylgroup, a benzo[c][1,2,5]thiadiazolyl group, a5,10-dihydrodibenzo[b,e][1,4]azasilinyl, a pyrazolo[1,5-c]quinazolinylgroup, a pyrido[1,2-b]indazolyl group, apyrido[1,2-a]imidazo[1,2-e]indolinyl group, a5,11-dihydroindeno[1,2-b]carbazolyl group, etc., but are not limitedthereto.

In the present specification, the amine group may be selected from thegroup comprising a monoalkylamine group; a monoarylamine group; amonoheteroarylamine group; —NH₂; a dialkylamine group; a diarylaminegroup; a diheteroarylamine group; an alkylarylamine group; analkylheteroarylamine group; and an arylheteroarylamine group, and thenumber of carbon atoms thereof is not particularly limited, but ispreferably 1 to 30. Specific examples of the amine group may comprise amethylamine group, a dimethylamine group, an ethylamine group, adiethylamine group, a phenylamine group, a naphthylamine group, abiphenylamine group, a dibiphenylamine group, an anthracenylamine group,a 9-methyl-anthracenylamine group, a diphenylamine group, aphenylnaphthylamine group, a ditolylamine group, a phenyltolylaminegroup, a triphenylamine group, a biphenylnaphthylamine group, aphenylbiphenylamine group, a biphenylfluorenylamine group, aphenyltriphenylenylamine group, a biphenyltriphenylenylamine group,etc., but are not limited thereto.

In the present specification, the arylene group means that the arylgroup has two bonding positions, that is, a divalent group. Thedescription of the aryl group described above may be applied except thateach of these is a divalent group. Further, the heteroarylene groupmeans that the heteroaryl group has two bonding positions, that is, adivalent group. The description of the heteroaryl group described abovemay be applied except that each of these is a divalent group.

In the present specification, the phosphine oxide group is representedby —P(═O)R101R102, and R101 and R102 may be the same as or differentfrom each other and may be each independently a substituent comprisingat least one of hydrogen; deuterium; a halogen group; an alkyl group; analkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and aheterocyclic group. Specifically, it may be substituted with an arylgroup, and the above-described examples may be applied to the arylgroup. For example, the phosphine oxide group comprises adiphenylphosphine oxide group, a dinaphthylphosphine oxide group, etc.,but is not limited thereto.

In the present specification, the silyl group may be a substituent whichcomprises Si, and to which the Si atom is directly connected as aradical, and is represented by —SiR104R105R106, and R104 to R106 may bethe same as or different from each other and may be each independently asubstituent comprising at least one of hydrogen; deuterium; a halogengroup; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkylgroup; an aryl group; and a heterocyclic group. Specific examples of thesilyl group may comprise a trimethylsilyl group, a triethylsilyl group,a t-butyldimethylsilyl group, a vinyldimethylsilyl group, apropyldimethylsilyl group, a triphenylsilyl group, a diphenylsilylgroup, a phenylsilyl group, etc., but are not limited thereto.

In the present specification, the “adjacent” group may mean asubstituent substituted on an atom directly connected to the atom inwhich the corresponding substituent is substituted, a substituentpositioned to be sterically closest to the corresponding substituent, oranother substituent substituted on the atom in which the correspondingsubstituent is substituted. For example, two substituents substituted atan ortho position in a benzene ring and two substituents substituted atthe same carbon in an aliphatic ring may be interpreted as groups“adjacent” to each other.

The structures exemplified by the above-described cycloalkyl group,cycloheteroalkyl group, aryl group and heteroaryl group may be appliedexcept that the aliphatic or aromatic hydrocarbon ring or heterocyclering that adjacent groups may form is not a monovalent group.

An embodiment of the present application provides an organic lightemitting device comprising a first electrode, a second electrode, and anorganic material layer comprising one or more layers provided betweenthe first electrode and the second electrode, wherein the one or morelayers of the organic material layer comprise a heterocyclic compoundrepresented by Chemical Formula 1 above and a heterocyclic compoundrepresented by Chemical Formula 2 above.

In an embodiment of the present application, Chemical Formula 1 abovemay be represented by Chemical Formula 3 or 4 below.

In Chemical Formulas 3 and 4 above, the definition of each substituentis the same as defined in Chemical Formula 1 above.

In an embodiment of the present application,

of Chemical Formula 1 above may be represented by any one of ChemicalFormulas 1-1 to 1-3 below.

In Chemical Formulas 1-1 to 1-3 above,

means a position connected to Chemical Formula 1, and

the definition of each substituent is the same as defined in ChemicalFormula 1 above.

In an embodiment of the present application, X may be O; or S.

In an embodiment of the present application, X may be O.

In an embodiment of the present application, X may be S.

In an embodiment of the present application, X1 to X3 may be N; or CRe,and at least one of X1 to X3 may be N.

In an embodiment of the present application, X1 to X3 may be N.

In an embodiment of the present application, X1 and X2 may be N, and X3may be CRe.

In an embodiment of the present application, X1 and X3 may be N, and X2may be CRe.

In an embodiment of the present application, R1 to R8, and Rc and Rd maybe the same as or different from each other, and may be eachindependently selected from the group comprising hydrogen; deuterium; ahalogen; a cyano group; a substituted or unsubstituted C1-C60 alkylgroup; a substituted or unsubstituted C2-C60 alkenyl group; asubstituted or unsubstituted C2-C60 alkynyl group; a substituted orunsubstituted C1-C60 alkoxy group; a substituted or unsubstituted C3-C60cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkylgroup; a substituted or unsubstituted C6-C60 aryl group; a substitutedor unsubstituted C2-C60 heteroaryl group; —SiRR′R″; —P(═O)RR′; and—NRR′, or two or more groups adjacent to each other may be bonded toeach other to form a substituted or unsubstituted aromatic hydrocarbonring or a substituted or unsubstituted heterocycle ring.

In another embodiment, R1 to R8, and Rc and Rd may be the same as ordifferent from each other and may be each independently selected fromthe group comprising hydrogen; deuterium; a substituted or unsubstitutedC1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; asubstituted or unsubstituted C2-C60 heteroaryl group; —SiRR′R″;—P(═O)RR′; and —NRR′.

In another embodiment, R1 to R8, and Rc and Rd may be the same as ordifferent from each other and may be each independently hydrogen;deuterium; a substituted or unsubstituted C1-C60 alkyl group; asubstituted or unsubstituted C6-C60 aryl group; or a substituted orunsubstituted C2-C60 heteroaryl group.

In another embodiment, R1 to R8, and Rc and Rd may be the same as ordifferent from each other and may be each independently hydrogen;deuterium; a substituted or unsubstituted C1-C40 alkyl group; asubstituted or unsubstituted C6-C40 aryl group; or a substituted orunsubstituted C2-C40 heteroaryl group.

In another embodiment, R1 to R8, and Rc and Rd may be the same as ordifferent from each other and may be each independently hydrogen;deuterium; or a substituted or unsubstituted C6-C40 aryl group.

In another embodiment, R1 to R8, and Rc and Rd may be the same as ordifferent from each other and may be each independently hydrogen;deuterium; or a C6-C40 aryl group.

In another embodiment, R1 to R8, and Rc and Rd may be the same as ordifferent from each other and may be each independently hydrogen;deuterium; or a C6-C20 aryl group.

In another embodiment, R1 to R8, and Rc and Rd may be the same as ordifferent from each other and may be each independently hydrogen;deuterium; a monocyclic C6-C10 aryl group; or a polycyclic C10-C20 arylgroup.

In another embodiment, R1 to R8, and Rc and Rd may be the same as ordifferent from each other and may be each independently hydrogen;deuterium; a substituted or unsubstituted phenyl group; or a substitutedor unsubstituted biphenyl group.

In another embodiment, R1 to R8, and Rc and Rd may be the same as ordifferent from each other and may be each independently hydrogen;deuterium; a phenyl group; or a biphenyl group.

In an embodiment of the present application, Ar1 may be a substituted orunsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

In another embodiment, Ar1 may be a substituted or unsubstituted C6-C60aryl group.

In another embodiment, Ar1 may be a substituted or unsubstituted C6-C40aryl group.

In another embodiment, Ar1 may be a C6-C40 aryl group.

In another embodiment, Ar1 may be a monocyclic C6-C10 aryl group; or apolycyclic C10-C40 aryl group.

In another embodiment, Ar1 may be a monocyclic C6-C10 aryl group; or apolycyclic C10-C20 aryl group.

In another embodiment, Ar1 may be a substituted or unsubstituted phenylgroup; or a substituted or unsubstituted biphenyl group.

In another embodiment, Ar1 may be a phenyl group; or a biphenyl group.

In another embodiment, Ar1 may be represented by any one of ChemicalFormulas 1-1-1 to 1-1-3 below.

In Chemical Formulas 1-1-1 to 1-1-3 above,

means a position connected to Chemical Formula 1.

In an embodiment of the present application, L1 may be a direct bond; asubstituted or unsubstituted C6-C60 arylene group; or a substituted orunsubstituted C2-C60 heteroarylene group.

In another embodiment, L1 may be a direct bond; a substituted orunsubstituted C6-C40 arylene group; or a substituted or unsubstitutedC2-C40 heteroarylene group.

In another embodiment, L1 may be a direct bond; or a substituted orunsubstituted C6-C40 arylene group.

In another embodiment, L1 may be a direct bond; or a C6-C40 arylenegroup.

In another embodiment, L1 may be a direct bond; or a C6-C20 arylenegroup.

In another embodiment, L1 may be a direct bond; a substituted orunsubstituted phenylene group; or a substituted or unsubstitutedbiphenylene group.

In another embodiment, L1 may be a direct bond; a phenylene group; or abiphenylene group.

In an embodiment of the present application, Ar2 may be a substituted orunsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

In another embodiment, Ar2 may be a substituted or unsubstituted C1-C40alkyl group; a substituted or unsubstituted C6-C40 aryl group; or asubstituted or unsubstituted C2-C40 heteroaryl group.

In another embodiment, Ar2 may be a substituted or unsubstituted C6-C40aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

In another embodiment, Ar2 may be a C6-C40 aryl group; or a C2-C40heteroaryl group.

In another embodiment, Ar2 may be a substituted or unsubstituted phenylgroup; a substituted or unsubstituted biphenyl group; a substituted orunsubstituted terphenyl group; a substituted or unsubstitutedtriphenylenyl group; a substituted or unsubstituted dibenzofuran group;or a substituted or unsubstituted dibenzothiophene group.

In another embodiment, Ar2 may be a phenyl group; a biphenyl group; aterphenyl group; a triphenylenyl group; a dibenzofuran group; or adibenzothiophene group.

In another embodiment, Ar2 may be represented by Chemical Formula 1-2-1or 1-2-2 below.

In Chemical Formulas 1-2-1 and 1-2-2 above,

q is the same as the definition in Chemical Formula 1 above,

means a position connected to Chemical Formula 1,

X1 is O; or S,

R11 to R15 are the same as or different from each other, and are eachindependently selected from the group comprising hydrogen; deuterium; ahalogen; a cyano group; a substituted or unsubstituted C1-C60 alkylgroup; a substituted or unsubstituted C2-C60 alkenyl group; asubstituted or unsubstituted C2-C60 alkynyl group; a substituted orunsubstituted C1-C60 alkoxy group; a substituted or unsubstituted C3-C60cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkylgroup; a substituted or unsubstituted C6-C60 aryl group; a substitutedor unsubstituted C2-C60 heteroaryl group; —SiRR′R″; —P(═O)RR′; and—NRR′, or two or more groups adjacent to each other are bonded to eachother to form a substituted or unsubstituted aromatic hydrocarbon ringor a substituted or unsubstituted heterocycle ring,

a1 is an integer of 0 to 3, and when it is 2 or more, the substituentsin parentheses are the same as or different from each other,

the definitions of R, R′, and R″ are the same as those in ChemicalFormula 1 above, and

Ar11 is a substituted or unsubstituted C6-C60 aryl group.

In an embodiment of the present application, R11 to R15 may be the sameas or different from each other, and may be each independently selectedfrom the group comprising hydrogen; deuterium; a halogen; a cyano group;a substituted or unsubstituted C1-C60 alkyl group; a substituted orunsubstituted C2-C60 alkenyl group; a substituted or unsubstitutedC2-C60 alkynyl group; a substituted or unsubstituted C1-C60 alkoxygroup; a substituted or unsubstituted C3-C60 cycloalkyl group; asubstituted or unsubstituted C2-C60 heterocycloalkyl group; asubstituted or unsubstituted C6-C60 aryl group; a substituted orunsubstituted C2-C60 heteroaryl group; —SiRR′R″; —P(═O)RR′; and —NRR′,or two or more groups adjacent to each other may be bonded to each otherto form a substituted or unsubstituted aromatic hydrocarbon ring or asubstituted or unsubstituted heterocycle ring.

In another embodiment, R11 to R15 may be the same as or different fromeach other, and may be each independently selected from the groupcomprising hydrogen; deuterium; a substituted or unsubstituted C1-C60alkyl group; a substituted or unsubstituted C6-C60 aryl group; and asubstituted or unsubstituted C2-C60 heteroaryl group, or two or moregroups adjacent to each other may be bonded to each other to form asubstituted or unsubstituted aromatic hydrocarbon ring or a substitutedor unsubstituted heterocycle ring.

In another embodiment, R11 to R15 may be the same as or different fromeach other, and may be each independently selected from the groupcomprising hydrogen; deuterium; a substituted or unsubstituted C1-C60alkyl group; a substituted or unsubstituted C6-C60 aryl group; and asubstituted or unsubstituted C2-C60 heteroaryl group.

In another embodiment, R11 to R15 may be the same as or different fromeach other, and may be each independently selected from the groupcomprising hydrogen; deuterium; a C1-C60 alkyl group; a C6-C60 arylgroup; and a C2-C60 heteroaryl group.

In another embodiment, R11 to R15 may be the same as or different fromeach other, and may be each independently selected from the groupcomprising hydrogen; deuterium; a C1-C40 alkyl group; a C6-C40 arylgroup; and a C2-C40 heteroaryl group.

In another embodiment, R11 to R15 may be the same as or different fromeach other, and may be each independently selected from the groupcomprising hydrogen; deuterium; a C6-C40 aryl group; and a C2-C40heteroaryl group.

In another embodiment, R11 to R15 may be the same as or different fromeach other, and may be each independently hydrogen; or deuterium.

In an embodiment of the present application, Ar11 is a substituted orunsubstituted C6-C60 aryl group.

In another embodiment, Ar11 is a substituted or unsubstituted C6-C40aryl group.

In another embodiment, Ar11 is a C6-C40 aryl group.

In another embodiment, Ar11 is a C6-C20 aryl group.

In another embodiment, Ar11 is a C6-C10 monocyclic aryl group; or aC10-C20 polycyclic aryl group.

In another embodiment, Ar11 may be a C6-C10 substituted or unsubstitutedphenyl group; a substituted or unsubstituted biphenyl group; asubstituted or unsubstituted terphenyl group; or a substituted orunsubstituted triphenylenyl group.

In another embodiment, Ar11 may be a C6-C10 phenyl group; a biphenylgroup; a terphenyl group; or a triphenylenyl group.

In an embodiment of the present application, Chemical Formula 1-2-2above may be represented by any one of Chemical Formulas 1-A to 1-Dbelow.

In Chemical Formulas 1-A to 1-D above,

the definition of each substituent is the same as the definition inChemical Formula 1-2-2 above.

In an embodiment of the present application, L2 may be a direct bond; asubstituted or unsubstituted C6-C60 arylene group; or a substituted orunsubstituted C2-C60 heteroarylene group.

In another embodiment, L2 may be a direct bond; a substituted orunsubstituted C6-C40 arylene group; or a substituted or unsubstitutedC2-C40 heteroarylene group.

In another embodiment, L2 may be a direct bond; a C6-C40 arylene group;or a C2-C40 heteroarylene group.

In another embodiment, L2 may be a direct bond; a substituted orunsubstituted phenylene group; a substituted or unsubstitutedbiphenylene group; or a substituted or unsubstituted divalentdibenzofuran group.

In another embodiment, L2 may be a direct bond; a phenylene group; abiphenylene group; or a divalent dibenzofuran group.

In an embodiment of the present application, Ra and Rb may be the sameas or different from each other, and may be each independently —CN;SiRR′R″; a substituted or unsubstituted C6-C60 aryl group; or asubstituted or unsubstituted C2-C60 heteroaryl group.

In another embodiment, Ra may be —CN; SiRR′R″; a substituted orunsubstituted C6-C60 aryl group; or a substituted or unsubstitutedC2-C60 heteroaryl group.

In another embodiment, Ra may be —CN; SiRR′R″; a C6-C40 aryl groupsubstituted or unsubstituted with a C1-C40 alkyl group or a C6-C40 arylgroup; or a C2-C60 heteroaryl group substituted or unsubstituted with aC6-C40 aryl group.

In another embodiment, Ra may be —CN; SiRR′R″; a substituted orunsubstituted phenyl group; a substituted or unsubstituted biphenylgroup; a substituted or unsubstituted terphenyl group; a substituted orunsubstituted dimethylfluorenyl group; a substituted or unsubstituteddiphenylfluorenyl group; a substituted or unsubstituted spirobifluorenylgroup; or a substituted or unsubstituted dibenzofuran group.

In another embodiment, Ra may be —CN; SiRR′R″; a phenyl group; abiphenyl group; a terphenyl group; a dimethylfluorenyl group; adiphenylfluorenyl group; a spirobifluorenyl group; or a dibenzofurangroup substituted or unsubstituted with a phenyl group.

In another embodiment, Rb may be a substituted or unsubstituted C6-C60aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

In another embodiment, Rb may be a C6-C60 aryl group substituted orunsubstituted with a C1-C40 alkyl group, —CN, SiRR′R″, or a C6-C40 arylgroup.

In another embodiment, Rb may be a C6-C40 aryl group substituted orunsubstituted with a C1-C40 alkyl group, —CN, SiRR′R″, or a C6-C40 arylgroup.

In another embodiment, Rb may be a phenyl group substituted orunsubstituted with —CN or SiRR′R″; a biphenyl group substituted orunsubstituted with a phenyl group; a terphenyl group; and adimethylfluorenyl group.

In an embodiment of the present application, -(L2)a-Ra and Rb ofChemical Formula 2 above may be different from each other.

In an embodiment of the present application, -(L2)a-Ra and Rb ofChemical Formula 2 above may be the same as each other.

In an embodiment of the present application, Re may be hydrogen;deuterium; a substituted or unsubstituted C1-C60 alkyl group; or asubstituted or unsubstituted C6-C60 aryl group.

In another embodiment, Re may be hydrogen; or deuterium.

In an embodiment of the present application, R, R′, and R″ may be thesame as or different from each other and may be each independently asubstituted or unsubstituted C1-C60 alkyl group; a substituted orunsubstituted C6-C60 aryl group; or a substituted or unsubstitutedC2-C60 heteroaryl group.

In another embodiment, R, R′, and R″ may be the same as or differentfrom each other and may be each independently a substituted orunsubstituted C1-C60 alkyl group; or a substituted or unsubstitutedC6-C60 aryl group.

In another embodiment, R, R′, and R″ may be the same as or differentfrom each other and may be each independently a C1-C60 alkyl group; or aC6-C60 aryl group.

In another embodiment, R, R′, and R″ may be the same as or differentfrom each other and may be each independently a methyl group; or aphenyl group.

In another embodiment, R, R′, and R″ may be a substituted orunsubstituted phenyl group.

In another embodiment, R, R′, and R″ may be a substituted orunsubstituted methyl group.

In another embodiment, R, R′, and R″ may be a phenyl group.

When the compound of Chemical Formula 1 above and the compound ofChemical Formula 2 above are simultaneously included in the organicmaterial layer of the organic light emitting device, better efficiencyand lifespan effects are exhibited. This result may expect an exciplexphenomenon to occur when both compounds are included at the same time.

The exciplex phenomenon is a phenomenon in which energy having a size ofa HOMO level of a donor (p-host) and a LUMO level of an acceptor(n-host) is emitted through electron exchange between two molecules.When a donor (p-host) with good hole transport ability and an acceptor(n-host) with good electron transport ability are used as a host of thelight emitting layer, since holes are injected into the p-host andelectrons are injected into the n-host, the driving voltage may belowered, thereby helping to improve the lifespan.

According to an embodiment of the present application, Chemical Formula1 above may be represented by any one of compounds below, but is notlimited thereto.

In an embodiment of the present application, Chemical Formula 2 abovemay be represented by any one of compounds below, but is not limitedthereto.

Further, compounds having intrinsic properties of the introducedsubstituents may be synthesized by introducing various substituents intothe structures of Chemical Formulas 1 and 2 above. For example,materials satisfying the conditions required in each organic materiallayer may be synthesized by introducing into the core structure thesubstituents mainly used for a hole injection layer material, a holetransport layer material, a light emitting layer material, an electrontransport layer material, and a charge generation layer material usedduring manufacturing of an organic light emitting device.

Further, various substituents are introduced into the structures ofChemical Formulas 1 and 2 above so that the energy band gap can befinely controlled, whereas the properties at the interface betweenorganic materials may be improved, and the use of the material may bediversified.

Meanwhile, the heterocyclic compound has a high glass transitiontemperature (Tg) to have excellent thermal stability. Such an increasein thermal stability becomes an important factor providing drivingstability to the device.

The heterocyclic compound according to an embodiment of the presentapplication may be prepared by a multi-step chemical reaction. Someintermediate compounds are prepared first, and compounds of ChemicalFormula 1 or 2 may be prepared from the intermediate compounds. Morespecifically, the heterocyclic compound according to an embodiment ofthe present application may be prepared based on Preparation Examples tobe described later.

Further, another embodiment of the present application provides acomposition for the organic material layer of the organic light emittingdevice, comprising the heterocyclic compound represented by ChemicalFormula 1 above and the heterocyclic compound represented by ChemicalFormula 2 above.

Specific details of the heterocyclic compound represented by ChemicalFormula 1 above and the heterocyclic compound represented by ChemicalFormula 2 above are the same as described above.

The weight ratio of the heterocyclic compound represented by ChemicalFormula 1 above to the heterocyclic compound represented by ChemicalFormula 2 above in the composition may be 1:10 to 10:1, 1:8 to 8:1, 1:5to 5:1, and 1:2 to 2:1, but is not limited thereto.

The composition may be used when forming an organic material of anorganic light emitting device, and in particular, it may be morepreferably used when forming a host of a light emitting layer.

The composition is a form in which two or more compounds are simplymixed, and a material in a powder state may be mixed before forming anorganic material layer of an organic light emitting device, or acompound in a liquid state at an appropriate temperature or higher maybe mixed. The composition is in a solid state at a melting point orlower of each material, and may be maintained in a liquid state if thetemperature is adjusted.

The composition may further comprise materials known in the art such assolvents, additives, etc.

The organic light emitting device according to an embodiment of thepresent application may be manufactured by conventional manufacturingmethod and material of the organic light emitting device except that oneor more organic material layers are formed using the heterocycliccompound represented by Chemical Formula 1 and the heterocyclic compoundrepresented by Chemical Formula 2 described above.

The heterocyclic compound represented by Chemical Formula 1 above andthe heterocyclic compound represented by Chemical Formula 2 above may beformed into an organic material layer by a solution application methodas well as a vacuum deposition method when manufacturing an organiclight emitting device. Here, the solution application method refers tospin coating, dip coating, inkjet printing, screen printing, spraying,roll coating, etc., but is not limited thereto.

The organic material layer of the organic light emitting device of thepresent disclosure may be formed in a single-layer structure, but may beformed in a multilayer structure in which two or more organic materiallayers are stacked. For example, the organic light emitting device ofthe present disclosure may have a structure comprising a hole injectionlayer, a hole transport layer, a light emitting layer, an electrontransport layer, an electron injection layer, etc. as an organicmaterial layer. However, the structure of the organic light emittingdevice is not limited thereto and may comprise a smaller number oforganic material layers.

Specifically, the organic light emitting device according to anembodiment of the present application comprises a first electrode, asecond electrode, and an organic material layer comprising one or morelayers provided between the first electrode and the second electrode,wherein the one or more layers of the organic material layer comprise aheterocyclic compound represented by Chemical Formula 1 above and aheterocyclic compound represented by Chemical Formula 2 above.

In an embodiment of the present application, the first electrode may bean anode, and the second electrode may be a cathode.

In another embodiment, the first electrode may be a cathode, and thesecond electrode may be an anode.

In an embodiment of the present application, the organic light emittingdevice may be a blue organic light emitting device, and the heterocycliccompound according to Chemical Formula 1 above and the heterocycliccompound according to Chemical Formula 2 above may be used as a materialof the blue organic light emitting device.

In an embodiment of the present application, the organic light emittingdevice may be a green organic light emitting device, and theheterocyclic compound represented by Chemical Formula 1 above and theheterocyclic compound represented by Chemical Formula 2 above may beused as a material of the green organic light emitting device.

In an embodiment of the present application, the organic light emittingdevice may be a red organic light emitting device, and the heterocycliccompound represented by Chemical Formula 1 above and the heterocycliccompound represented by Chemical Formula 2 above may be used as amaterial of the red organic light emitting device.

The organic light emitting device of the present disclosure may furthercomprise one layer or two or more layers selected from the groupcomprising a light emitting layer, a hole injection layer, a holetransport layer, an electron injection layer, an electron transportlayer, an electron blocking layer, and a hole blocking layer.

In an embodiment of the present application, there is provided anorganic light emitting device in which the organic material layercomprises at least one layer of a hole blocking layer, an electroninjection layer, and an electron transport layer, and the at least onelayer of the hole blocking layer, the electron injection layer, and theelectron transport layer comprises a heterocyclic compound representedby Chemical Formula 1 above and a heterocyclic compound represented byChemical Formula 2 above.

In an embodiment of the present application, there is provided anorganic light emitting device in which the organic material layercomprises a light emitting layer, and the light emitting layer comprisesa heterocyclic compound represented by Chemical Formula 1 above and aheterocyclic compound represented by Chemical Formula 2 above.

In an embodiment of the present application, there is provided anorganic light emitting device in which the organic material layercomprises a light emitting layer, the light emitting layer comprises ahost material, and the host material comprises a heterocyclic compoundrepresented by Chemical Formula 1 above and a heterocyclic compoundrepresented by Chemical Formula 2 above.

FIGS. 1 to 3 exemplify a lamination order of electrodes and organicmaterial layers of an organic light emitting device according to anembodiment of the present application. However, it is not intended thatthe scope of the present application be limited by these drawings, andthe structure of an organic light emitting device known in the art mayalso be applied to the present application.

Referring to FIG. 1 , an organic light emitting device in which an anode200, an organic material layer 300, and a cathode 400 are sequentiallylaminated on a substrate 100 is illustrated. However, it is not limitedto such a structure, and as shown in FIG. 2 , an organic light emittingdevice in which a cathode, an organic material layer, and an anode aresequentially laminated on a substrate may also be implemented.

FIG. 3 exemplifies a case in which the organic material layer ismultiple layers. The organic light emitting device according to FIG. 3comprises a hole injection layer 301, a hole transport layer 302, alight emitting layer 303, a hole blocking layer 304, an electrontransport layer 305, and an electron injection layer 306. However, thescope of the present application is not limited by such a laminationstructure, the remaining layers except for the light emitting layer asneeded may be omitted, and other necessary functional layers may befurther added.

In an embodiment of the present application, there is provided a methodfor manufacturing an organic light emitting device, comprising the stepsof: preparing a substrate; forming a first electrode on the substrate;forming an organic material layer comprising one or more layers on thefirst electrode; and forming a second electrode on the organic materiallayer, wherein the step of forming the organic material layer comprisesa step of forming an organic material layer comprising one or morelayers using the composition for the organic material layer according toan embodiment of the present application.

In an embodiment of the present application, there is provided a methodfor manufacturing an organic light emitting device, in which the step offorming the organic material layer is forming the organic material layerusing a thermal vacuum deposition method by premixing the heterocycliccompound of Chemical Formula 1 above and the heterocyclic compound ofChemical Formula 2 above.

The premixing refers to mixing the premixed materials in the containerafter premixing materials and putting the premixed materials into onecontainer before depositing the heterocyclic compound of ChemicalFormula 1 above and the heterocyclic compound of Chemical Formula 2above on the organic material layer.

The premixed materials may be referred to as the composition for theorganic material layer according to an embodiment of the presentapplication.

In the organic light emitting device according to an embodiment of thepresent application, although materials other than the heterocycliccompound of Chemical Formula 1 above and the heterocyclic compound ofChemical Formula 2 above are exemplified below, these are forillustration only, not for limiting the scope of the presentapplication, and may be replaced with materials known in the art.

As an anode material, materials having a relatively high work functionmay be used, and transparent conductive oxides, metals, conductivepolymers, or the like may be used. Specific examples of the anodematerial may comprise metals such as vanadium, chromium, copper, zinc,and gold, or alloys thereof; metal oxides such as zinc oxide, indiumoxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al orSnO₂: combinations of metals such as Sb and oxides; conductive polymerssuch as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline; etc., but are not limitedthereto.

As a cathode material, materials having a relatively low work functionmay be used, and metals, metal oxides, conductive polymers, or the likemay be used. Specific examples of the cathode material may comprisemetals such as magnesium, calcium, sodium, potassium, titanium, indium,yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloysthereof; a multilayered material such as LiF/Al or LiO₂/Al; etc., butare not limited thereto.

As a hole injection material, known hole injection materials may beused. For example, a phthalocyanine compound such as copperphthalocyanine or the like disclosed in U.S. Pat. No. 4,356,429, orstarburst-type amine derivatives disclosed in the literature [AdvancedMaterial, 6, p. 677 (1994)] such as tris(4-carbazolyl-9-ylphenyl)amine(TCTA), 4,4,4-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA),1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), asoluble conductive polymer Polyaniline/Dodecylbenzenesulfonic acid orPoly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate),Polyaniline/Camphor sulfonic acid,Polyaniline/Poly(4-styrene-sulfonate), or the like may be used.

As a hole transport material, pyrazoline derivatives, arylamine-basedderivatives, stilbene derivatives, triphenyldiamine derivatives, etc.may be used, and low molecular weight or high molecular weight materialsmay also be used.

As an electron transport material, metal complexes of oxadiazolederivatives, anthraquinodimethane and its derivatives, benzoquinone andits derivatives, naphthoquinone and its derivatives, anthraquinone andits derivatives, tetracyanoanthraquinodimethane and its derivatives,fluorenone derivatives, diphenyldicyanoethylene and its derivatives,diphenoquinone derivatives, and 8-hydroxyquinoline and its derivativesmay be used, and high molecular weight materials as well as lowmolecular weight materials may also be used.

As an electron injection material, for example, LiF is typically used inthe art, but the present application is not limited thereto.

As a light emitting material, a red, green, or blue light emittingmaterial may be used, and if necessary, two or more light emittingmaterials may be mixed and used. At this time, two or more lightemitting materials may be deposited and used as individual sources, ormay be premixed and deposited as a single source and used. Further, afluorescent material may be used as a light emitting material, but aphosphorescent material may also be used. As the light emittingmaterial, a material that emits light by combining holes and electronsrespectively injected from the anode and the cathode may be used alone,but materials in which the host material and the dopant materialtogether involve in light emission may also be used.

When mixing and using the host of the light emitting material, hosts ofthe same series may be mixed and used, or hosts of different series maybe mixed and used. For example, any two or more types of n-type hostmaterials and p-type host materials may be selected and used as a hostmaterial of the light emitting layer.

The organic light emitting device according to an embodiment of thepresent application may be a top emission type, a back emission type, ora double side emission type depending on materials used.

A heterocyclic compound according to an embodiment of the presentapplication may act on a principle similar to that applied to an organiclight emitting device even in an organic electronic device comprising anorganic solar cell, an organic photoreceptor, an organic transistor,etc.

Hereinafter, the present specification will be described in more detailthrough Examples, but these are only for exemplifying the presentapplication and not for limiting the scope of the present application.

[Preparation Example 1] Preparation of Compound 1-81 (C-1)

Preparation of Compound 1-81

10 g (34.7 mmol) of (4-(dibenzo[b,d]furan-4-yl)phenyl)boronic acid, 17.5g (41.6 mmol) of 2,4-di([1,1′-biphenyl]-4-yl)-6-chloro-1,3,5-triazine, 4g (3.5 mmol) of tetrakis(triphenylphosphine)palladium(0), 14.4 g (104.1mmol) of potassium carbonate, and a 1,4-dioxane/water mixture (100 ml/20ml) were refluxed in an one neck round bottom flask at 120° C. for 3hours. When the reaction was completed, the temperature was lowered toroom temperature, and a reaction product was washed with 1,4-dioxane,distilled water, and MeOH to obtain Compound 1-81 (18 g, 82%).

In Preparation Example 1 above, Target Compound (C-1) was synthesized byperforming the synthesis process in the same manner as in PreparationExample 1 above except that Compound A-1 of Table 1 below was usedinstead of (4-(dibenzo[b,d]furan-4-yl)phenyl)boronic acid, and CompoundB of Table 1 below was used instead of2,4-di([1,1′-biphenyl]-4-yl)-6-chloro-1,3,5-triazine.

TABLE 1 Com- Yield pound A-1 B C-1 (%) 1-82

52 1-86

63 1-91

72 1-96

75 1-98

68 1-102

80 1-107

65 1-111

45 1-120

77 1-128

71

[Preparation Example 2] Preparation of Compound 1-129 (C-2)

Preparation of Compound 1-129

10 g (32.9 mmol) of (4-(dibenzo[b,d]thiophen-4-yl)phenyl)boronic acid,16.5 g (39.5 mmol) of2,4-di([1,1′-biphenyl]-4-yl)-6-chloro-1,3,5-triazine, 3.8 g (3.3 mmol)of tetrakis(triphenylphosphine)palladium(0), 13.6 g (98.6 mmol) ofpotassium carbonate, and a 1,4-dioxane/water mixture (100 ml/20 ml) wererefluxed in an one neck round bottom flask at 120° C. for 3 hours. Afterperforming filtration at 120° C., a reaction product was washed with1,4-dioxane, distilled water, and MeOH at 120° C. to obtain Compound1-129 (15 g, 70%).

In Preparation Example 2 above, Target Compound (C-2) was synthesized byperforming the synthesis process in the same manner as in PreparationExample 2 above except that Compound A-2 of Table 2 below was usedinstead of (4-(dibenzo[b,d]furan-4-yl)phenyl)boronic acid, and CompoundB of Table 2 below was used instead of2,4-di([1,1′-biphenyl]-4-yl)-6-chloro-1,3,5-triazine.

TABLE 2 Com- Yield pound A-2 B C-2 (%) 1-130

52 1-134

63 1-139

72 1-144

75 1-146

68 1-150

80 1-155

65 1-159

75 1-168

64 1-176

74

[Preparation Example 3] Preparation of Compound 1-1 (C-3)

Synthesis Method of Intermediate 1

After putting 20 g (61.88 mmol) of4-(4-bromophenyl)dibenzo[b,d]furan(A), 31.4 g (123.7 mmol) ofbis(pinacolate)diboron, 4.52 g (6.18 mmol) of Pd(dppf)Cl₂, and 18.2 g(185.64 mmol) of KOA_(c) into a reaction flask and putting 1,4-dioxanethereinto, the materials were refluxed at 120° C. for 3 hours. When thereaction was completed, the temperature was lowered to room temperature,the reaction solution was extracted with MC and H₂O, and the organiclayer was purified by column to obtain Intermediate 1 (18 g, 81%).

Synthesis Method of Compound 1-1 (C-3)

After putting 18 g (48.6 mmol) of Intermediate 1, 20 g (58.3 mmol) of2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine, 2.8 g (2.43mmol) of Pd(PPh₃)₄, and 20.1 g (145.8 mmol) of K₂CO₃ into a reactionflask and putting a 1,4-dioxane/water mixture (180 ml/45 ml) thereinto,the materials were heated at 120° C. for 4 hours. After completing thereaction, the temperature was lowered to room temperature, and theresulting solid was washed with distilled water and MeOH to obtainCompound 1-1 (C-3) (20 g, 74%).

In Preparation Example 3 above, Compound (C-3) below was synthesized inthe same manner except that Compounds A-3 and B of Table 3 below wereused.

TABLE 3 Yield Compound A-3 B C-3 (%) 1-2

74 1-12

80 1-17

83 1-21

88 1-22

82 1-32

80 1-37

87 1-41

85 1-42

87 1-52

81 1-57

80 1-61

86 1-62

84 1-72

85 1-77

86

[Preparation Example 4] Preparation of Compound 1-3 (C-4)

Synthesis Method of Intermediate 2

After putting 20 g (71 mmol) of 2-bromo-6-chlorodibenzo[b,d]furan, 17.3g (142 mmol) of phenylboronic acid, 8.2 g (7.1 mmol) of Pd(PPh₃)₄, and29.4 g (213 mmol) of K₂CO₃ into a reaction flask and putting a1,4-dioxane/water mixture (200 ml/50 ml) thereinto, the materials wereheated at 120° C. for 4 hours. After completing the reaction, thetemperature was lowered to room temperature, and the resulting solid waswashed with distilled water and MeOH to obtain Intermediate 2 (15 g,76%).

Synthesis Method of Intermediate 3

After putting 15 g (53.8 mmol) of Intermediate 2, 12.9 g (64.5 mmol) of(4-bromophenyl)boronic acid, 0.91 g (2.69 mmol) of Pd(dba)₂, 22.3 g(161.4 mmol) of K₂CO₃, and 2.51 g (5.38 mmol) of Xphos into a reactionflask and putting a 1,4-dioxane/water mixture (150 ml/37.5 ml)thereinto, the materials were heated at 120° C. for 4 hours. Aftercompleting the reaction, the temperature was lowered to roomtemperature, and the resulting solid was washed with distilled water andMeOH to obtain Intermediate 3 (15 g, 70%).

Synthesis Method of Intermediate 4

It was synthesized in the same manner as in Synthesis Method ofIntermediate 1 of Preparation Example 3 above.

Synthesis Method of Compound 1-3 (C-4)

It was synthesized in the same manner as in Synthesis Method of Compound1-1 (C-3) of Preparation Example 3 above.

Compound (C-4) below was synthesized in the same manner except thatCompounds A-4, I, and B of Table 4 below were used.

TABLE 4 Com- Yield pound A-4 I B C-4 (%) 1-4

75 1-5

83 1-6

85 1-7

83 1-8

84 1-9

85 1-10

83 1-11

80 1-13

87 1-15

81 1-16

80 1-19

87 1-23

85 1-24

86 1-25

87 1-26

88 1-27

80 1-28

89 1-29

80 1-30

80 1-31

81 1-33

82 1-38

83 1-39

84 1-43

85 1-44

86 1-45

87 1-46

80 1-47

81 1-48

82 1-49

83 1-50

84 1-51

80 1-53

81 1-58

82 1-59

86 1-63

84 1-64

82 1-65

82 1-66

83 1-67

84 1-68

82 1-69

82 1-70

83 1-71

84 1-73

82 1-78

83 1-79

82

<Preparation Example 5> Synthesis of Compound 2-3

1) Preparation of Compound 2-3

3.7 g (15.8 mM) of 3-bromo-1,1′-biphenyl, 6.5 g (15.8 mM) of9-phenyl-9H,9′H-3,3′-bicarbazole, 3.0 g (15.8 mM) of CuI, 1.9 mL (15.8mM) of trans-1,2-diaminocyclohexane, and 3.3 g (31.6 mM) of K₃PO₄ weredissolved in 100 mL of 1,4-oxane and then refluxed for 24 hours. Afterthe reaction was completed, distilled water and DCM were put at roomtemperature for extraction, the organic layer was dried with MgSO₄, andthe solvent was removed by a rotary evaporator. The reaction product waspurified by column chromatography (DCM:Hex=1:3) and recrystallized withmethanol to obtain 7.5 g (85%) of Target Compound 2-3.

The target Compound A was synthesized by preparing Target Compound A inthe same manner as in the preparation of Preparation Example 5 exceptthat Intermediate A of Table 5 below was used instead of3-bromo-1,1″-biphenyl, and Intermediate B of Table 5 below was usedinstead of 9-phenyl-9H,9′H-3,3′-bicarbazole in Preparation Example 5above.

TABLE 5 Com - pound Intermediate Intermediate Target Total No. A BCompound A yield 2-4

83% 2-7

84%  2-16

80%  2-31

81%  2-32

80%  2-34

74%  2-42

82%  2-71

84%

The heterocyclic compounds of Chemical Formulas 1 and 2 other than thecompounds shown in Tables 1 to 5 above were also prepared in the samemanner as described in the above-mentioned Preparation Examples.

Synthesis confirmation data of the compounds prepared above are as shownin [Table 6] and [Table 7] below.

TABLE 6 Compound FD-Mass Compound FD-Mass 1-1 m/z = 551.64 (C39H25N3O =551.20) 1-2 m/z = 551.64 (C39H25N3O = 551.20) 1-3 m/z = 627.73(C45H29N3O = 627.23) 1-4 m/z = 627.73 (C45H29N3O = 627.23) 1-5 m/z =627.73 (C45H29N3O = 627.23) 1-6 m/z = 627.73 (C45H29N3O = 627.23) 1-7m/z = 627.73 (C45H29N3O = 627.23) 1-8 m/z = 627.73 (C45H29N3O = 627.23)1-9 m/z = 717.81 (C51H31N3O2 = 717.24)  1-10 m/z = 717.81 (C51H31N3O2 =717.24)  1-11 m/z = 717.81 (C51H31N3O2 = 717.24)  1-12 m/z = 551.64(C39H25N3O = 551.20)  1-13 m/z = 627.73 (C45H29N3O = 627.23)  1-14 m/z =733.88 (C51H31N3OS = 733.22)  1-15 m/z = 733.88 (C51H31N3OS = 733.22) 1-16 m/z = 733.88 (C51H31N3OS = 733.22)  1-17 m/z = 551.64 (C39H25N3O =551.20)  1-18 m/z = 717.81 (C51H31N3O2 = 717.24)  1-19 m/z = 717.81(C51H31N3O2 = 717.24)  1-20 m/z = 733.88 (C51H31N3OS = 733.22)  1-21 m/z= 551.64 (C39H25N3O = 551.20)  1-22 m/z = 551.64 (C39H25N3O = 551.20) 1-23 m/z = 627.73 (C45H29N3O = 627.23)  1-24 m/z = 627.73 (C45H29N3O =627.23)  1-25 m/z = 627.73 (C45H29N3O = 627.23)  1-26 m/z = 627.73(C45H29N3O = 627.23)  1-27 m/z = 627.73 (C45H29N3O = 627.23)  1-28 m/z =627.73 (C45H29N3O = 627.23)  1-29 m/z = 717.81 (C51H31N3O2 = 717.24) 1-30 m/z = 717.81 (C51H31N3O2 = 717.24)  1-31 m/z = 717.81 (C51H31N3O2= 717.24)  1-32 m/z = 551.64 (C39H25N3O = 551.20)  1-33 m/z = 627.73(C45H29N3O = 627.23)  1-34 m/z = 733.88 (C51H31N3OS = 733.22)  1-35 m/z= 733.88 (C51H31N3OS = 733.22)  1-36 m/z = 733.88 (C51H31N3OS = 733.22) 1-37 m/z = 551.64 (C39H25N3O = 551.20)  1-38 m/z = 717.81 (C51H31N3O2 =717.24)  1-39 m/z = 717.81 (C51H31N3O2 = 717.24)  1-40 m/z = 733.88(C51H31N3OS = 733.22)  1-41 m/z = 567.70 (C39H25N3S = 567.18)  1-42 m/z= 567.70 (C39H25N3S = 567.18)  1-43 m/z = 643.80 (C45H29N3S = 643.21) 1-44 m/z = 643.80 (C45H29N3S = 643.21)  1-45 m/z = 643.80 (C45H29N3S =643.21)  1-46 m/z = 643.80 (C45H29N3S = 643.21)  1-47 m/z = 643.80(C45H29N3S = 643.21)  1-48 m/z = 643.80 (C45H29N3S = 643.21)  1-49 m/z =733.88 (C51H31N3OS = 733.22)  1-50 m/z = 733.88 (C51H31N3OS = 733.22) 1-51 m/z = 733.88 (C51H31N3OS = 733.22)  1-52 m/z = 567.70 (C39H25N3S =567.18)  1-53 m/z = 643.80 (C45H29N3S = 643.21)  1-54 m/z = 749.94(C51H31N3S2 = 749.20)  1-55 m/z = 749.94 (C51H31N3S2 = 749.20)  1-56 m/z= 749.94 (C51H31N3S2 = 749.20)  1-57 m/z = 567.70 (C39H25N3S = 567.18) 1-58 m/z = 733.88 (C51H31N3OS = 733.22)  1-59 m/z = 733.88 (C51H31N3OS= 733.22)  1-60 m/z = 749.94 (C51H31N3S2 = 749.20)  1-61 m/z = 567.70(C39H25N3S = 567.18)  1-62 m/z = 567.70 (C39H25N3S = 567.18)  1-63 m/z =643.80 (C45H29N3S = 643.21)  1-64 m/z = 643.80 (C45H29N3S = 643.21) 1-65 m/z = 643.80 (C45H29N3S = 643.21)  1-66 m/z = 643.80 (C45H29N3S =643.21)  1-67 m/z = 643.80 (C45H29N3S = 643.21)  1-68 m/z = 643.80(C45H29N3S = 643.21)  1-69 m/z = 733.88 (C51H31N3OS = 733.22)  1-70 m/z= 733.88 (C51H31N3OS = 733.22)  1-71 m/z = 733.88 (C51H31N3OS = 733.22) 1-72 m/z = 567.70 (C39H25N3S = 567.18)  1-73 m/z = 643.80 (C45H29N3S =643.21)  1-74 m/z = 749.94 (C51H31N3S2 = 749.20)  1-75 m/z = 749.94(C51H31N3S2 = 749.20)  1-76 m/z = 749.94 (C51H31N3S2 = 749.20)  1-77 m/z= 567.70 (C39H25N3S = 567.18)  1-78 m/z = 733.88 (C51H31N3OS = 733.22) 1-79 m/z = 733.88 (C51H31N3OS = 733.22)  1-80 m/z = 749.94 (C51H31N3S2= 749.20)  1-81 m/z = 627.73 (C45H29N3O = 627.23)  1-82 m/z = 627.73(C45H29N3O = 627.23)  1-83 m/z = 703.83 (C51H33N3O = 703.26)  1-84 m/z =627.73 (C45H29N3O = 627.23)  1-85 m/z = 627.73 (C45H29N3O = 627.23) 1-86 m/z = 779.92 (C57H374N3O = 779.29)  1-87 m/z = 701.81 (C51H31N3O =701.25)  1-88 m/z = 627.73 (C45H29N3O = 627.23)  1-89 m/z = 703.83(C51H33N3O = 703.26)  1-90 m/z = 703.83 (C51H33N3O = 703.26)  1-91 m/z =641.71 (C45H27N4O2 = 641.21)  1-92 m/z = 657.78 (C45H27N3OS = 657.19) 1-93 m/z = 641.71 (C45H27N4O2 = 641.21)  1-94 m/z = 627.73 (C45H29N3O =627.23)  1-95 m/z = 703.83 (C51H33N3O = 703.26)  1-96 m/z = 627.73(C45H29N3O = 627.23)  1-97 m/z = 703.83 (C51H33N3O = 703.26)  1-98 m/z =701.81 (C51H31N3O = 701.25)  1-99 m/z = 703.83 (C51H33N3O = 703.26) 1-100 m/z = 703.83 (C51H33N3O = 703.26)  1-101 m/z = 703.83 (C51H33N3O= 703.26)  1-102 m/z = 641.71 (C45H27N4O2 = 641.21)  1-103 m/z = 641.71(C45H27N4O2 = 641.21)  1-104 m/z = 657.78 (C45H27N3OS = 657.19)  1-105m/z = 627.73 (C45H29N3O = 627.23)  1-106 m/z = 627.73 (C45H29N3O =627.23)  1-107 m/z = 703.83 (C51H33N3O = 703.26)  1-108 m/z = 627.73(C45H29N3O = 627.23)  1-109 m/z = 627.73 (C45H29N3O = 627.23)  1-110 m/z= 779.92 (C57H374N3O = 779.29)  1-111 m/z = 701.81 (C51H31N3O = 701.25) 1-112 m/z = 627.73 (C45H29N3O = 627.23)  1-113 m/z = 703.83 (C51H33N3O= 703.26)  1-114 m/z = 703.83 (C51H33N3O = 703.26)  1-115 m/z = 641.71(C45H27N4O2 = 641.21)  1-116 m/z = 657.78 (C45H27N3OS = 657.19)  1-117m/z = 641.71 (C45H27N4O2 = 641.21)  1-118 m/z = 627.73 (C45H29N3O =627.23)  1-119 m/z = 703.83 (C51H33N3O = 703.26)  1-120 m/z = 627.73(C45H29N3O = 627.23)  1-121 m/z = 703.83 (C51H33N3O = 703.26)  1-122 m/z= 701.81 (C51H31N3O = 701.25)  1-123 m/z = 703.83 (C51H33N3O = 703.26) 1-124 m/z = 703.83 (C51H33N3O = 703.26)  1-125 m/z = 703.83 (C51H33N3O= 703.26)  1-126 m/z = 641.71 (C45H27N4O2 = 641.21)  1-127 m/z = 641.71(C45H27N4O2 = 641.21)  1-128 m/z = 657.78 (C45H27N3OS = 657.19)  1-129m/z = 627.73 (C45H29N3O = 627.23)  1-130 m/z = 627.73 (C45H29N3O =627.23)  1-131 m/z = 703.83 (C51H33N3O = 703.26)  1-132 m/z = 627.73(C45H29N3O = 627.23)  1-133 m/z = 627.73 (C45H29N3O = 627.23)  1-134 m/z= 779.92 (C57H374N3O = 779.29)  1-135 m/z = 701.81 (C51H31N3O = 701.25) 1-136 m/z = 627.73 (C45H29N3O = 627.23)  1-137 m/z = 703.83 (C51H33N3O= 703.26)  1-138 m/z = 703.83 (C51H33N3O = 703.26)  1-139 m/z = 641.71(C45H27N4O2 = 641.21)  1-140 m/z = 657.78 (C45H27N3OS = 657.19)  1-141m/z = 641.71 (C45H27N4O2 = 641.21)  1-142 m/z = 627.73 (C45H29N3O =627.23)  1-143 m/z = 703.83 (C51H33N3O = 703.26)  1-144 m/z = 627.73(C45H29N3O = 627.23)  1-145 m/z = 703.83 (C51H33N3O = 703.26)  1-146 m/z= 701.81 (C51H31N3O = 701.25)  1-147 m/z = 703.83 (C51H33N3O = 703.26) 1-148 m/z = 703.83 (C51H33N3O = 703.26)  1-149 m/z = 703.83 (C51H33N3O= 703.26)  1-150 m/z = 641.71 (C45H27N4O2 = 641.21)  1-151 m/z = 641.71(C45H27N4O2 = 641.21)  1-152 m/z = 657.78 (C45H27N3OS = 657.19)  1-153m/z = 643.80 (C45H29N3S = 643.21)  1-154 m/z = 643.80 (C45H29N3S =643.21)  1-155 m/z = 719.89 (C51H33N3S = 719.24)  1-156 m/z = 643.80(C45H29N3S = 643.21)  1-157 m/z = 643.80 (C45H29N3S = 643.21)  1-158 m/z= 795.99 (C57H37N3S = 795.27)  1-159 m/z = 717.88 (C51H31N3S = 717.22) 1-160 m/z = 643.80 (C45H29N3S = 643.21)  1-161 m/z = 719.89 (C51H33N3S= 719.24)  1-162 m/z = 719.89 (C51H33N3S = 719.24)  1-163 m/z = 657.78(C45H27N3OS = 657.19)  1-164 m/z = 678.85 (C45H27N3S2 = 673.16)  1-165m/z = 657.78 (C45H27N3OS = 657.19)  1-166 m/z = 643.80 (C45H29N3S =643.21)  1-167 m/z = 719.89 (C51H33N3S = 719.24)  1-168 m/z = 643.80(C45H29N3S = 643.21)  1-169 m/z = 719.89 (C51H33N3S = 719.24)  1-170 m/z= 717.88 (C51H31N3S = 717.22)  1-171 m/z = 719.89 (C51H33N3S = 719.24) 1-172 m/z = 719.89 (C51H33N3S = 719.24)  1-173 m/z = 703.83 (C51H33N3O= 703.26)  1-174 m/z = 641.71 (C45H27N3O2 = 641.21)  1-175 m/z = 641.71(C45H27N3O2 = 641.21)  1-176 m/z = 657.78 (C45H27N3OS = 657.19) 2-1 m/z= 484.19 (C₃₆H₂₄N₂ = 484.60) 2-2 m/z = 560.23 (C₄₂H₂₈N₂ = 560.70) 2-3m/z = 560.23 (C₄₂H₂₈N₂ = 560.70) 2-4 m/z = 560.23 (C₄₂H₂₈N₂ = 560.70)2-5 m/z = 636.26 (C₄₈H₃₂N₂ = 636.80) 2-6 m/z = 636.26 (C₄₈H₃₂N₂ =636.80) 2-7 m/z = 636.26 (C₄₈H₃₂N₂ = 636.80) 2-8 m/z = 585.69 (C43H20N3= 585.22) 2-9 m/z = 661.79(C49H31N3 = 661.25)  2-10 m/z = 600.26(C₄₅H₃₂N₂ = 600.76)  2-11 m/z = 600.26 (C₄₅H₃₂N₂ = 600.76)  2-12 m/z =724.29 (C₅₅H₃₆N₂ = 724.91)  2-13 m/z = 724.29 (C₅₅H₃₆N₂ = 724.91)  2-14m/z = 722.27 (C₅₅H₃₄N₂ = 722.89)  2-15 m/z = 722.27 (C₅₅H₃₄N₂ = 722.89) 2-16 m/z = 650.76 (C48H30N2O = 650.24)  2-17 m/z = 509.19 (C₃₇H₂₃N₃ =509.61)  2-18 m/z = 742.28 (C₅₄H₃₈N₂Si = 743.00)  2-19 m/z = 636.26(C₄₈H₃₂N₂ = 636.80)  2-20 m/z = 636.26 (C₄₈H₃₂N₂ = 636.80)  2-21 m/z =636.26 (C₄₈H₃₂N₂ = 636.80)  2-22 m/z = 712.29 (C₅₄H₃₆N₂ = 712.90)  2-23m/z = 712.29 (C₅₄H₃₆N₂ = 712.90)  2-24 m/z = 712.29 (C₅₄H₃₆N₂ = 712.90) 2-25 m/z = 661.79 (C49H31N3 = 661.25)  2-26 m/z = 726.86(C54H34N2O =726.27)  2-27 m/z = 676.29 (C₅₁H₃₆N₂ = 676.86)  2-28 m/z = 710.27(C₅₄H₃₄N₂ = 710.88)  2-29 m/z = 585.22 (C₄₃H₂₇N₃ = 585.71)  2-30 m/z =818.31 (C₆₀H₄₂N₂Si = 819.10)  2-31 m/z = 636.26 (C₄₈H₃₂N₂ = 636.80) 2-32 m/z = 636.26 (C₄₈H₃₂N₂ = 636.80)  2-33 m/z = 712.29 (C₅₄H₃₆N₂ =712.90)  2-34 m/z = 712.29 (C₅₄H₃₆N₂ = 712.90)  2-35 m/z = 712.29(C₅₄H₃₆N₂ = 712.90)  2-36 m/z = 650.76 (C48H30N2O = 650.24)  2-37 m/z =650.76 (C48H30N4O2 = 650.24)  2-38 m/z = 676.29 (C₅₁H₃₆N₂ = 676.86) 2-39 m/z = 650.76 (C48H30N2O = 650.24)  2-40 m/z = 585.22 (C₄₃H₂₇N₃ =585.71)  2-41 m/z = 818.31 (C₆₀H₄₂N₂Si = 819.10)  2-42 m/z = 636.26(C₄₈H₃₂N₂ = 636.80)  2-43 m/z = 712.29 (C₅₄H₃₆N₂ = 712.90)  2-44 m/z =712.29 (C₅₄H₃₆N₂ = 712.90)  2-45 m/z = 712.29 (C₅₄H₃₆N₂ = 712.90)  2-46m/z = 726.86 (C54H34N2O = 726.27)  2-47 m/z = 726.86 (C₅₄H₃₄N₂O =610.76)  2-48 m/z = 676.29 (C₅₁H₃₆N₂ = 676.86)  2-49 m/z = 661.79(C₄₉H₃₁N₃ = 661.25)  2-50 m/z = 585.22 (C₄₃H₂₇N₃ = 585.71)  2-51 m/z =818.31 (C₆₀H₄₂N₂Si = 819.10)  2-52 m/z = 788.32 (C₆₀H₄₀N₂ = 788.99) 2-53 m/z = 788.32 (C₆₀H₄₀N₂ = 788.99)  2-54 m/z = 788.32 (C₆₀H₄₀N₂ =788.99)  2-55 m/z = 895.17 (C₆₆H₄₆N₂Si = 894.34)  2-56 m/z = 716.91(C₅₄H₄₀N₂ = 716.32)  2-57 m/z = 752.32 (C₅₇H₄₀N₂ = 752.96)  2-58 m/z =625.76 (C₄₆H₃₁N₃ = 625.25)  2-59 m/z = 661.25 (C₄₉H₃₁N₃ = 661.81)  2-60m/z = 894.34 (C₆₆H₄₆N₂Si = 895.19)  2-61 m/z = 788.32 (C₆₀H₄₀N₂ =788.99)  2-62 m/z = 788.32 (C₆₀H₄₀N₂ = 788.99)  2-63 m/z = 859.14(C₆₃H₄₆N₂Si = 858.34)  2-64 m/z = 534.61 (C₃₈H₂₂N₄ = 534.18)  2-65 m/z =752.32 (C₅₇H₄₀N₂ = 752.96)  2-66 m/z = 767.99 (C₅₅H₃₇N₃Si = 767.28) 2-67 m/z = 661.25 (C₄₉H₃₁N₃ = 661.81)  2-68 m/z = 894.34 (C₆₆H₄₆N₂Si =895.19)  2-69 m/z = 788.32 (C₆₀H₄₀N₂ = 788.99)  2-70 m/z = 1001.37(C₇₂H₅₂N₂Si₂ = 1000.37)  2-71 m/z = 712.88 (C₅₄H₃₆N₂ = 712.29)  2-72 m/z= 752.32 (C₅₇H₄₀N₂ = 752.96)

TABLE 7 Compound ¹H NMR(CDCl₃, 300 Hz) 1-1 δ = 8.22(d, 2H), 7.89-7.81(m,7H), 7.66(d, 1H), 7.52-7.25(m, 15H) 1-2 δ = 8.28-8.24(m, 3H),7.89-7.81(m, 5H), 7.70-7.66(m, 2H), 7.57-7.32(m, 15H) 1-3 δ = 8.28(m,2H), 7.85-7.81(m, 7H), 7.72-7.71(m, 2H), 7.52-7.38(m, 14H), 7.25(m, 4H)1-8 δ = 8.24-8.28(m, 3H), 7.85-7.70(m, 8H), 7.57-7.38(m, 16H)  1-10 δ =8.24(d, 1H), 7.95-7.32(m, 30H)  1-12 δ = 8.28-8.24(m, 3H), 7.89-7.81(m,5H), 7.70-7.66(m, 2H), 7.51-7.25(m, 15H)  1-17 δ = 8.28-8.24(m, 4H),7.89-7.81(m, 3H), 7.70-7.66(m, 3H), 7.57-7.32(m, 15H)  1-23 δ = 8.28(m,2H), 7.95(d, 1H), 7.85-7.71(m, 8H), 7.64(s, 1H), 7.52-7.41(m, 13H),7.25(m, 4H)  1-24 δ = 8.28-8.24(m, 3H), 7.95(m, 1H), 7.85-7.70(m, 7H),7.64(s, 1H), 7.57-7.41(m, 15H), 7.25(d, 2H)  1-26 δ = 8.28(d, 2H),7.89-7.79(m, 7H), 7.60-7.25(m, 20H)  1-29 δ = 7.95-7.64(m, 15H),7.52-7.25(m, 16H)  1-33 δ = 8.28-8.24(m, 3H), 7.89-7.79(m, 5H),7.70-7.25(m, 21H)  1-39 δ = 8.24(d, 1H), 7.95-7.25(m, 31H)  1-41 δ =8.45-8.41(m, 2H), 8.28(m, 2H), 8.20(m, 1H), 7.98(m, 1H), 7.85(m, 4H),7.58-7.41(m, 11H), 7.25(m, 4H)  1-43 δ = 8.41(d,lH), 8.28(m, 2H),8.20(d, 1H), 8.00(d, 2H), 7.86-7.85(m, 5H), 7.58-7.41(m, 14H), 7.25(m,4H)  1-44 δ = 8.41(d, 1H), 8.28-8.20(m, 4H), 8.00(d, 2H), 7.8-7.85(m,3H), 7.58-7.41(m, 16H), 7.25(m, 2H)  1-68 δ = 8.28-8.24(m, 3H),8.11-8.05(m, 3H), 7.94(d, 1H), 7.85-7.79(m, 5H), 7.70(s, 1H),7.57-7.41(m, 14H), 7.25(d, 2H)  1-72 δ = 8.45(d, 1H), 8.28-8.24(m, 3H),8.11-7.98(m, 4H), 7.85(m, 2H), 7.70(s, 1H), 7.57-7.48(m, 12H), 7.25(m,2H)  1-81 δ = 7.89-7.81(m, 9H), 7.66(d, 1H), 7.52-7.25(m, 19H)  1-87 δ =9.15(s, 1H), 8.93(d, 2H), 8.18-8.12(m, 3H), 8.04(d, 1H), 7.89-7.81(m,11H), 7.66(d, 1H), 7.51-7.25(m, 12H)  1-92 δ = 8.45(d, 1H), 8.11-8.08(m,2H), 7.98(d, 1H), 7.89-7.81(m, 8H), 7.66(d, 1H), 7.52-7.25(m, 14H)  1-98δ = 9.15(s, 1H), 8.93(d, 2H), 8.24-8.04(m, 5H), 7.89-7.81(m, 9H),7.70-7.66(m, 2H), 7.57-7.25(m, 12H)  1-102 δ = 8.24(d, 2H), 7.95-7.89(m,4H), 7.70-7.64(m, 10H), 7.52-7.32(m, 11H)  1-153 δ = 8.45-8.41(m, 2H),8.20(m, 1H), 7.98(m, 1H), 7.85(m, 6H), 7.58-7.41(m, 13H), 7.25(m, 6H) 1-166 δ = 8.24(m, 2H), 7.89-7.85(m, 3H), 7.57-7.25(m, 24H)  1-173 δ =8.24(m, 2H), 7.89-7.85(m, 3H), 7.70-7.25(m, 28H) 2-3 δ = 8.55(1H, d),8.3O(1H, d), 8.21-8.13(3H, m), 7.99-7.89(4H, m), 7.77-7.35(17H, m),7.20-7.16(2H, m) 2-4 δ = 8.55(1H, d), 8.30(1H, d), 8.19-8.13(2H, m),7.99-7.89(8H, m), 7.77-7.75(3H, m), 7.62-7.35(11H, m), 7.20-7.16(2H, m)2-7 δ = 8.55(1H, d), 8.31-8.30(3H, d), 8.19-8.13(2H, m), 7.99-7.89(5H,m), 7.77-7.75(5H, m), 7.62-7.35(14H, m), 7.20-7.16(2H, m)  2-16 δ =8.93-8.90(3H, d), 8.55(1H, d), 8.18-8.10(5H, m), 8.00-7.77(10H, m),7.58-7.45(8H, m), 7.33-7.29(2H, m)  2-31 δ = 8.55(1H, d), 8.30(1H, d),8.21-8.13(4H, m), 7.99-7.89(4H, m), 7.77-7.35(20H, m), 7.20-7.16(2H, m) 2-32 δ = 8.55(1H, d),8.30(1H, d), 8.21-8.13(3H, m), 7.99-7.89(8H, m),7.77-7.35(17H, m), 7.20-7.16(2H, m)  2-34 δ = 8.55(1H, d),8.18-8.09(3H,m), 8.00-7.94(2H, m), 7.87(1H, d), 7.79-7.77(4H, m), 7.69-7.63(4H,m),7.51-7.25(21H, m)  2-42 δ = 8.55(1H, d),8.18-8.12(2H, m), 8.00-7.87(3H,m), 7.79-7,77(6H, m), 7.69-7.63(6H, m), 7.52-7.25(14H, m)

<Experimental Example 1>—Fabrication of Organic Light Emitting Devices

1) Fabrication of Organic Light Emitting Devices

Glass substrates coated with a thin film of ITO to a thickness of 1,500Å were washed with distilled water and ultrasonic waves. After washingthe substrates with distilled water, ultrasonic cleaning was performedon the washed substrates with solvents such as acetone, methanol,isopropyl alcohol, etc., the ultrasonic cleaned substrates were dried,and WO-treated for 5 minutes using UV in a UV cleaner. Thereafter, aftertransferring the substrates to a plasma cleaner (PT), plasma treatmentwas performed to remove the ITO work function and residual film in avacuum state, and the substrates were transferred to thermal depositionequipment for organic deposition.

As common layers on the ITO transparent electrodes (anodes), a holeinjection layer 2-TNATA(4,4′,4″-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a holetransport layer NPB(N,N′-Di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine) wereformed.

A light emitting layer was thermal vacuum deposited thereon as follows.The light emitting layer was deposited to a thickness of 400 Å by dopingthe host with 7% of Ir(ppy)₃ using the compounds shown in Table 8 belowas a host and Ir(ppy)₃ (tris(2-phenylpyridine)iridium) as a greenphosphorescent dopant. Thereafter, BCP was deposited to a thickness of60 Å as a hole blocking layer, and Alq₃ was deposited to a thickness of200 Å thereon as an electron transport layer. Finally, after forming anelectron injection layer by depositing lithium fluoride (LiF) to athickness of 10 Å on the electron transport layer, an aluminum (Al)cathode was deposited to a thickness of 1,200 Å on the electroninjection layer to form cathodes, thereby manufacturing organicelectroluminescent devices.

Meanwhile, all organic compounds required for fabricating OLED deviceswere vacuum sublimated and purified under 10⁻⁶ to 10⁻⁸ torr for eachmaterial respectively, and used for OLED fabrication.

2) Driving Voltage and Luminous Efficiency of Organic ElectroluminescentDevices

Electroluminescence (EL) characteristics were measured for the organicelectroluminescent devices fabricated as described above with M7000 ofMcScience, and T₉₀ values were measured with the measurement resultswhen the reference luminance was 6,000 cd/m² through the device lifespanmeasuring system (M6000) manufactured by McScience. The properties ofthe organic electroluminescent devices of the present disclosure were asshown in Table 8.

TABLE 8 Driving Color voltage Yield coordinate Lifespan Compound (V)(cd/A) (x, y) (T₉₀) Comparative 1-1 4.28 65.3 (0.277, 0.669) 138 Example1  Comparative 1-2 4.26 66.7 (0.281, 0.679) 139 Example 2  Comparative1-3 4.12 63.2 (0.280, 0.677) 137 Example 3  Comparative 1-4 4.20 67.8(0.279, 0.676) 138 Example 4  Comparative 1-5 4.22 68.9 (0.272, 0.669)139 Example 5  Comparative 1-6 4.28 69.0 (0.271, 0.671) 140 Example 6 Comparative 1-7 4.29 66.7 (0.275, 0.672) 141 Example 7  Comparative 1-84.21 67.8 (0.279, 0.675) 141 Example 8  Comparative 1-9 4.18 69.1(0.280, 0.676) 138 Example 9  Comparative  1-10 4.17 70.1 (0.278, 0.672)139 Example 10 Comparative  1-11 4.15 63.2 (0.283, 0.687) 140 Example 11Comparative  1-12 4.23 64.5 (0.286, 0.686) 141 Example 12 Comparative 1-13 4.17 65.5 (0.274, 0.678) 140 Example 13 Comparative  1-15 4.1566.7 (0.279, 0.677) 141 Example 14 Comparative  1-17 4.10 67.8 (0.278,0.677) 141 Example 15 Comparative  1-19 4.18 69.2 (0.276, 0.671) 139Example 16 Comparative  1-21 4.18 69.9 (0.284, 0.687) 138 Example 17Comparative  1-22 4.19 68.9 (0.281, 0.684) 139 Example 18 Comparative 1-23 4.20 68.8 (0.283, 0.681) 138 Example 19 Comparative  1-24 4.2169.2 (0.279, 0.681) 137 Example 20 Comparative  1-25 4.08 77.3 (0.280,0.679) 142 Example 21 Comparative  1-26 4.07 78.8 (0.281, 0.678) 146Example 22 Comparative  1-27 4.00 78.9 (0.278, 0.682) 148 Example 23Comparative  1-28 4.06 72.3 (0.286, 0.692) 148 Example 24 Comparative 1-29 3.98 77.4 (0.274, 0.672) 149 Example 25 Comparative  1-30 3.9678.3 (0.278, 0.678) 150 Example 26 Comparative  1-31 3.99 79.2 (0.277,0.674) 147 Example 27 Comparative  1-32 3.92 80.4 (0.279, 0.674) 149Example 28 Comparative  1-33 4.08 80.3 (0.278, 0.677) 151 Example 29Comparative  1-34 4.09 81.2 (0.283, 0.677) 150 Example 30 Comparative 1-35 4.11 81.4 (0.273, 0.678) 151 Example 31 Comparative  1-36 4.0780.7 (0.277, 0.668) 152 Example 32 Comparative  1-37 3.88 83.1 (0.271,0.673) 157 Example 33 Comparative  1-38 3.89 84.7 (0.276, 0.671) 158Example 34 Comparative  1-39 3.87 83.9 (0.272, 0.666) 159 Example 35Comparative  1-40 3.85 82.9 (0.274, 0.667) 160 Example 36 Comparative 1-41 4.26 68.9 (0.279, 0.676) 137 Example 37 Comparative  1-48 4.2869.7 (0.272, 0.669) 138 Example 38 Comparative  1-52 4.18 67.7 (0.271,0.671) 139 Example 39 Comparative  1-58 4.16 69.9 (0.275, 0.672) 141Example 40 Comparative  1-61 3.92 78.9 (0.279, 0.675) 150 Example 41Comparative  1-63 3.90 79.2 (0.280, 0.676) 149 Example 42 Comparative 1-77 3.82 85.0 (0.277, 0.669) 149 Example 43 Comparative  1-78 3.8384.7 (0.281, 0.679) 151 Example 44 Comparative  1-81 4.16 68.7 (0.280,0.677) 138 Example 45 Comparative  1-82 4.18 69.2 (0.279, 0.676) 138Example 46 Comparative  1-83 4.13 69.3 (0.272, 0.669) 137 Example 47Comparative  1-84 4.21 67.2 (0.271, 0.671) 132 Example 48 Comparative 1-85 4.22 70.3 (0.275, 0.672) 137 Example 49 Comparative  1-88 4.1869.7 (0.279, 0.675) 135 Example 50 Comparative  1-89 4.17 71.2 (0.280,0.676) 136 Example 51 Comparative  1-90 4.18 70.3 (0.278, 0.672) 134Example 52 Comparative  1-92 4.15 69.4 (0.283, 0.687) 138 Example 53Comparative  1-93 4.11 69.9 (0.286, 0.686) 139 Example 54 Comparative 1-97 4.24 71.9 (0.274, 0.678) 137 Example 55 Comparative  1-99 4.2270.3 (0.279, 0.677) 136 Example 56 Comparative  1-101 3.99 78.9 (0.278,0.677) 150 Example 57 Comparative  1-102 3.97 77.3 (0.276, 0.671) 149Example 58 Comparative  1-103 3.99 78.8 (0.273, 0.678) 148 Example 59Comparative  1-104 3.98 79.2 (0.277, 0.668) 148 Example 60 Comparative 1-105 3.92 73.7 (0.271, 0.673) 147 Example 61 Comparative  1-106 3.9075.9 (0.276, 0.671) 149 Example 62 Comparative  1-108 3.91 76.6 (0.272,0.666) 148 Example 63 Comparative  1-113 3.89 76.7 (0.274, 0.667) 151Example 64 Comparative  1-114 3.90 77.7 (0.279, 0.676) 150 Example 65Comparative  1-115 3.88 79.2 (0.272, 0.669) 151 Example 66 Comparative 1-177 3.86 81.2 (0.271, 0.671) 158 Example 67 Comparative  1-118 3.8583.4 (0.275, 0.672) 159 Example 68 Comparative  1-119 3.87 82.9 (0.280,0.676) 159 Example 69 Comparative  1-120 3.88 84.0 (0.278, 0.672) 161Example 70 Comparative  1-125 4.12 70.2 (0.283, 0.687) 134 Example 71Comparative  1-128 4.18 69.3 (0.286, 0.686) 137 Example 72 Comparative 1-130 4.17 68.8 (0.274, 0.678) 139 Example 73 Comparative  1-141 3.9777.3 (0.279, 0.677) 149 Example 74 Comparative  1-143 3.92 78.8 (0.278,0.677) 148 Example 75 Comparative  1-145 3.94 79.2 (0.276, 0.671) 144Example 76 Comparative  1-146 3.90 77.3 (0.273, 0.678) 149 Example 77Comparative  1-157 3.85 83.1 (0.277, 0.668) 153 Example 78 Comparative 1-158 3.88 82.2 (0.274, 0.678) 155 Example 79 Comparative  1-159 3.8781.4 (0.279, 0.677) 157 Example 80 Comparative  1-160 3.85 83.2 (0.278,0.677) 159 Example 81

<Experimental Example 2>—Fabrication of Organic Light Emitting Devices

Glass substrates coated with a thin film of ITO to a thickness of 1,500Å were washed with distilled water and ultrasonic waves. After washingthe substrates with distilled water, ultrasonic cleaning was performedon the washed substrates with solvents such as acetone, methanol,isopropyl alcohol, etc., the ultrasonic cleaned substrates were dried,and WO-treated for 5 minutes using UV in a UV cleaner. Thereafter, aftertransferring the substrates to a plasma cleaner (PT), plasma treatmentwas performed to remove the ITO work function and residual film in avacuum state, and the substrates were transferred to thermal depositionequipment for organic deposition.

As common layers on the ITO transparent electrodes (anodes), a holeinjection layer 2-TNATA(4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine) and a holetransport layer NPB(N,N′-di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine) wereformed.

A light emitting layer was thermal vacuum deposited thereon as follows.The light emitting layer was deposited to a thickness of 400 Å on onecontainer after premixing one compound described in Chemical Formula 1and one compound described in Chemical Formula 2 in Table 9 below as ahost, and the green phosphorescent dopant was deposited by dopingIr(ppy)₃ to a thickness corresponding to 7% of the deposition thicknessof the light emitting layer. Thereafter, BCP was deposited to athickness of 60 Å as a hole blocking layer, and Alq₃ was deposited to athickness of 200 Å thereon as an electron transport layer. Finally,after forming an electron injection layer by depositing lithium fluoride(LiF) to a thickness of 10 A on the electron transport layer, analuminum (Al) cathode was deposited to a thickness of 1,200 Å on theelectron injection layer to form cathodes, thereby manufacturing organicelectroluminescent devices.

Meanwhile, all organic compounds required for fabricating OLED deviceswere vacuum sublimated and purified under 10⁻⁶ to 10⁻⁸ torr for eachmaterial respectively, and used for OLED fabrication.

Electroluminescence (EL) characteristics were measured for the organicelectroluminescent devices fabricated as described above with M7000 ofMcScience, and T₉₀ values were measured with the measurement resultswhen the reference luminance was 6,000 cd/m² through the device lifespanmeasuring system (M6000) manufactured by McScience.

The results of measuring driving voltage values, luminous efficiencyvalues, color coordinate (CIE) values, and lifespan values of theorganic light emitting devices manufactured according to the presentdisclosure were as shown in Table 9 below.

TABLE 9 Light emitting Driving layer voltage Efficiency Color coordinateLifespan compound Ratio (V) (cd/A) (x, y) (T₉₀) Example 1 1-1:2-5  1:3.53.81 125.3 (0.279, 0.677) 380 Example 2 1:3 3.80 127.6 (0.272, 0.666)378 Example 3 1:2 3.79 130.2 (0.274, 0.667) 377 Example 4  1-1:2-33 1:33.80 128.4 (0.277, 0.677) 381 Example 5 1:2 3.79 130.2 (0.277, 0.680)379 Example 6  1-1:2.24 1:3 3.72 140.6 (0.278, 0.681) 385 Example 7 1:23.70 144.4 (0.277, 0.682) 382 Example 8  1-1:2-53 1:3 3.73 142.3 (0.281,0.676) 384 Example 9 1:2 3.71 145.4 (0.280, 0.676) 380 Example 10 1-1:2-69 1:3 3.61 150.6 (0.276, 0.679) 390 Example 11 1:2 3.60 154.6(0.275, 0.679) 387 Example 12  1-1:2-72 1:3 3.63 153.7. (0.278, 0.678)389 Example 13 1:2 3.60 155.8 (0.279, 0.677) 385 Example 14  1-1:2-73 1:3.5 3.53 157.2 (0.275, 0.680) 393 Example 15 1:3 3.51 158.3 (0.274,0.678) 391 Example 16 1:2 3.50 160.6 (0.276, 0.676) 390 Example 17 1-1:2-15 1:3 3.51 155.6 (0.274, 0.679) 393 Example 18 1:2 3.50 161.7(0.288, 0.681) 390 Example 19  1-2:2-45  1:3.5 3.74 140.4 (0.278, 0.677)385 Example 20  1:2.5 3.71 143.7 (0.276, 0.671) 384 Example 21 1:2 3.70145.1 (0.273, 0.678) 381 Example 22  1-2:2-63 1:4 3.67 150.9 (0.277,0.668) 390 Example 23 1:3 3.62 153.7 (0.271, 0.673) 389 Example 24 1:2.5 3.60 155.9 (0.276, 0.671) 387 Example 25  1-2:2-49  1:3.5 3.56157.2 (0.272, 0.666) 393 Example 26  1:2.5 3.51 159.3 (0.274, 0.667) 393Example 27 1:2 3.50 160.2 (0.277, 0.677) 392 Example 28  1-2:2-40  1:3.53.54 156.4 (0.277, 0.680) 393 Example 29  1:2.5 3.52 158.3 (0.278,0.681) 392 Example 30 1:2 3.51 159.9 (0.277, 0.682) 390 Example 31 1-3:2-65 1:3 3.63 153.7 (0.276, 0.671) 390 Example 32 1:2 3.60 155.9(0.276, 0.671) 388 Example 33  1-3:2-33 1:3 3.52 157.9 (0.272, 0.666)393 Example 34 1:2 3.50 160.7 (0.274, 0.667) 392 Example 35  1-5:2-301:3 3.55 158.9 (0.273, 0.678) 393 Example 36 1:2 3.50 159.9 (0.277,0.668) 391 Example 37  1-5:2-44 1:3 3.53 157.9 (0.271, 0.673) 391Example 38 1:2 3.52 158.9 (0.276, 0.671) 390 Example 39  1-8:2-68  1:3.53.53 156.4 (0.272, 0.666) 393 Example 40  1:2.5 3.52 157.9 (0.274,0.667) 391 Example 41 1:2 3.50 159.9 (0.277, 0.677) 390 Example 42 1-8:2-34 1:3 3.52 156.7 (0.277, 0.680) 391 Example 43 1:2 3.51 158.9(0.278, 0.681) 390 Example 44 1-10:2-66 1:3 3.63 153.7 (0.277, 0.682)390 Example 45 1:2 3.62 155.2 (0.276, 0.671) 387 Example 46 1-10:2-381:3 3.53 156.7 (0.276, 0.671) 393 Example 47 1:2 3.50 159.9 (0.277,0.668) 391 Example 48 1-17:2-32 1:3 3.54 157.8 (0.271, 0.673) 393Example 49 1:2 3.52 159.9 (0.276, 0.671) 392 Example 50 1-17:2-13 1:33.53 156.7 (0.272, 0.666) 393 Example 51 1:2 3.50 159.9 (0.274, 0.667)392 Example 52 1-18:2-23 1:3 3.51 157.7 (0.277, 0.677) 393 Example 531:2 3.50 160.4 (0.277, 0.680) 390 Example 54 1-18:2-24 1:3 3.53 158.9(0.278, 0.681) 394 Example 55 1:2 3.52 160.7 (0.277, 0.682) 392 Example56 1-21:2-33 1:3 3.51 159.3 (0.276, 0.671) 393 Example 57 1:2 3.50 161.2(0.276, 0.671) 390 Example 58 1-22:2-5  1:3 3.71 143.3 (0.277, 0.677)443 Example 59 1:2 3.70 145.7 (0.277, 0.680) 380 Example 60 1-22:2-251:3 3.72 144.6 (0.276, 0.671) 385 Example 61 1:2 3.70 145.9 (0.272,0.666) 383 Example 62 1-22:2-42 1:3 3.63 154.3 (0.274, 0.667) 385Example 63 1:2 3.60 155.7 (0.277, 0.677) 381 Example 64 1-22:2-50 1:33.61 153.3 (0.277, 0.680) 390 Example 65 1:2 3.60 155.6 (0.278, 0.681)388 Example 66 1-22:2-66 1:3 3.53 158.7 (0.277, 0.682) 393 Example 671:2 3.50 160.3 (0.276, 0.671) 390 Example 68 1-22:2-72 1:3 3.52 157.9(0.276, 0.671) 394 Example 69 1:2 3.50 161.0 (0.277, 0.677) 391 Example70 1-22:2-33 1:3 3.43 168.7 (0.277, 0.680) 420 Example 71 1:2 3.41 169.3(0.276, 0.671) 418 Example 72 1-22:2-36 1:3 3.42 166.4 (0.272, 0.666)421 Example 73 1:2 3.40 170.2 (0.274, 0.667) 419 Example 74 1-23:2-101:3 3.43 167.7 (0.277, 0.677) 393 Example 75 1:2 3.42 170.3 (0.277,0.680) 382 Example 76 1-23:2-68 1:3 3.44 168.8 (0.277, 0.680) 420Example 77 1:2 3.41 170.2 (0.276, 0.671) 418 Example 78 1-24:2-64 1:33.51 158.9 (0.272, 0.666) 393 Example 79 1:2 3.50 160.2 (0.274, 0.667)391 Example 80 1-24:2-24 1:3 3.41 169.2 (0.277, 0.677) 421 Example 811:2 3.40 171.3 (0.277, 0.680) 419 Example 82 1-26:2-11 1:3 3.42 168.3(0.278, 0.681) 422 Example 83 1:2 3.40 170.9 (0.277, 0.682) 420 Example84 1-26:2-33 1:3 3.40 168.3 (0.276, 0.671) 421 Example 85 1:2 3.39 171.2(0.276, 0.671) 419 Example 86 1-27:2-24 1:3 3.41 169.9 (0.277, 0.677)420 Example 87 1:2 3.40 171.2 (0.277, 0.680) 419 Example 88 1-27:2-181:3 3.41 168.2 (0.276, 0.671) 422 Example 89 1:2 3.39 170.3 (0.272,0.666) 420 Example 90 1-37:2-22 1:3 3.53 158.2 (0.274, 0.667) 393Example 91 1:2 3.50 160.3 (0.277, 0.677) 391 Example 92 1-37:2-33 1:33.52 159.2 (0.278, 0.681) 394 Example 93 1:2 3.51 162.1 (0.277, 0.682)391 Example 94 1-37:2-45 1:3 3.42 168.2 (0.276, 0.671) 420 Example 951:2 3.40 170.3 (0.276, 0.671) 418 Example 96 1-37:2-55 1:3 3.41 169.2(0.277, 0.677) 422 Example 97 1:2 3.40 172.2 (0.277, 0.680) 420 Example98 1-37:2-65 1:3 3.32 178.2 (0.276, 0.671) 480 Example 99 1:2 3.30 180.3(0.272, 0.666) 478 Example 100 1-37:2-72 1:3 3.31 179.2 (0.274, 0.667)482 Example 101 1:2 3.30 181.1 (0.277, 0.677) 480 Example 102 1-37:2-731:3 3.21 188.3 (0.278, 0.681) 500 Example 103 1:2 3.20 190.2 (0.277,0.682) 492 Example 104 1-37:2-35 1:3 3.22 190.3 (0.276, 0.671) 500Example 105 1:2 3.20 192.7 (0.276, 0.671) 493 Example 106 1-39:2-31 1:33.18 190.7 (0.277, 0.677) 501 Example 107 1:2 3.16 192.2 (0.277, 0.680)499 Example 108 1-39:2-28 1:3 3.19 191.3 (0.277, 0.682) 500 Example 1091:2 3.17 193.2 (0.276, 0.671) 498 Example 110 1-39:2-30 1:3 3.20 190.7(0.276, 0.671) 502 Example 111 1:2 3.18 192.7 (0.277, 0.677) 500 Example112 1-41:2-43 1:3 3.50 158.8 (0.277, 0.680) 393 Example 113 1:2 3.48160.2 (0.272, 0.666) 391 Example 114 1-41:2-28 1:3 3.51 156.7 (0.277,0.680) 393 Example 115 1:2 3.50 159.3 (0.272, 0.666) 392 Example 1161-43:2-44 1:3 3.52 158.3 (0.274, 0.667) 394 Example 117 1:2 3.50 161.1(0.277, 0.677) 393 Example 118 1-43:2-30 1:3 3.50 158.8 (0.277, 0.680)394 Example 119 1:2 3.48 160.2 (0.272, 0.666) 393 Example 120 1-46:2-631:3 3.51 157.8 (0.279, 0.677) 392 Example 121 1:2 3.49 161.1 (0.277,0.680) 390 Example 122 1-46:2-43 1:3 3.50 159.2 (0.272, 0.666) 393Example 123 1:2 3.49 162.0 (0.279, 0.677) 390 Example 124 1-50:2-52 1:33.51 158.3 (0.279, 0.677) 392 Example 125 1:2 3.48 159.2 (0.277, 0.680)390 Example 126 1-50:2-61 1:3 3.51 157.3 (0.272, 0.666) 394 Example 1271:2 3.50 160.3 (0.279, 0.677) 392 Example 128 1-57:2-37 1:3 3.52 158.9(0.277, 0.668) 392 Example 129 1:2 3.51 160.1 (0.277, 0.680) 390 Example130 1-57:2-20 1:3 3.51 156.6 (0.272, 0.666) 391 Example 131 1:2 3.49159.9 (0.279, 0.677) 390 Example 132 1-61:2-71 1:3 3.40 168.3 (0.273,0.678) 422 Example 133 1:2 3.39 170.2 (0.277, 0.680) 420 Example 1341-61:2-33 1:3 3.38 169.8 (0.272, 0.666) 423 Example 135 1:2 3.37 171.1(0.279, 0.677) 421 Example 136 1-65:2-25 1:3 3.41 166.8 (0.277, 0.680)420 Example 137 1:2 3.39 170.2 (0.272, 0.666) 418 Example 138 1-65:2-641:3 3.40 169.7 (0.279, 0.677) 422 Example 139 1:2 3.38 172.5 (0.279,0.677) 420 Example 140 1-66:2-11 1:3 3.41 168.6 (0.277, 0.680) 422Example 141 1:2 3.40 170.5 (0.272, 0.666) 421 Example 142 1-66:2-23 1:33.39 171.4 (0.279, 0.677) 423 Example 143 1:2 3.38 172.3 (0.277, 0.668)420 Example 144 1-68:2-23 1:3 3.41 169.2 (0.277, 0.680) 422 Example 1451:2 3.40 171.6 (0.272, 0.666) 420 Example 146 1-68:2-33 1:3 3.41 168.6(0.279, 0.677) 423 Example 147 1:2 3.40 170.3 (0.273, 0.678) 421 Example148 1-77:2-58 1:3 3.21 188.6 (0.272, 0.666) 500 Example 149 1:2 3.20190.5 (0.277, 0.680) 495 Example 150 1-77:2-49 1:3 3.19 190.6 (0.272,0.666) 498 Example 151 1:2 3.18 192.5 (0.279, 0.677) 496 Example 1521-78:2-20 1:3 3.20 189.5 (0.277, 0.680) 499 Example 153 1:2 3.18 191.7(0.272, 0.666) 492 Example 154 1-78:2-33 1:3 3.21 187.7 (0.279, 0.677)498 Example 155 1:2 3.20 189.9 (0.279, 0.677) 497 Example 156 1-79:2-101:3 3.18 188.7 (0.277, 0.680) 499 Example 157 1:2 3.16 191.9 (0.272,0.666) 490 Example 158 1-79:2-28 1:3 3.21 187.8 (0.279, 0.677) 493Example 159 1:2 3.20 190.8 (0.277, 0.668) 490 Example 160 1-80:2-32 1:33.21 188.9 (0.277, 0.680) 501 Example 161 1:2 3.20 190.7 (0.272, 0.666)498 Example 162 1-80:2-53 1:3 3.19 191.5 (0.279, 0.677) 499 Example 1631:2 3.18 192.3 (0.273, 0.678) 492 Example 164 1-81:2-43 1:3 3.50 158.8(0.276, 0.676) 393 Example 165 1:2 3.48 160.2 (0.277, 0.668) 391 Example166 1-81:2-38 1:3 3.51 156.7 (0.277, 0.680) 393 Example 167 1:2 3.49159.3 (0.272, 0.666) 392 Example 168 1-83:2-22 1:3 3.50 158.3 (0.279,0.677) 394 Example 169 1:2 3.49 161.1 (0.273, 0.678) 393 Example 1701-83:2-47 1:3 3.51 158.8 (0.276, 0.676) 394 Example 171 1:2 3.48 160.2(0.277, 0.668) 393 Example 172 1-84:2-32 1:3 3.51 157.8 (0.277, 0.680)392 Example 173 1:2 3.50 161.1 (0.272, 0.666) 390 Example 174 1-84:2-291:3 3.52 159.2 (0.279, 0.677) 393 Example 175 1:2 3.51 162.0 (0.273,0.678) 390 Example 176 1-90:2-43 1:3 3.51 158.3 (0.276, 0.676) 392Example 177 1:2 3.49 159.2 (0.277, 0.668) 390 Example 178 1-90:2-38 1:33.50 157.3 (0.277, 0.680) 394 Example 179 1:2 3.48 160.3 (0.272, 0.666)392 Example 180 1-101:2-49  1:3 3.40 168.3 (0.279, 0.677) 422 Example181 1:2 3.39 170.2 (0.273, 0.678) 420 Example 182 1-101:2-27  1:3 3.38169.8 (0.276, 0.676) 423 Example 183 1:2 3.37 171.1 (0.277, 0.668) 421Example 184 1-101:2-17  1:3 3.41 166.8 (0.277, 0.680) 420 Example 1851:2 3.39 170.2 (0.272, 0.666) 418 Example 186 1-105:2-24  1:3 3.40 169.7(0.279, 0.677) 422 Example 187 1:2 3.38 172.5 (0.273, 0.678) 420 Example188 1-105:2-48  1:3 3.41 168.6 (0.276, 0.676) 422 Example 189 1:2 3.40170.5 (0.273, 0.678) 421 Example 190 1-105:2-66  1:3 3.39 171.4 (0.276,0.676) 423 Example 191 1:2 3.38 172.3 (0.277, 0.668) 420 Example 1921-105:2-58  1:3 3.41 169.2 (0.277, 0.680) 422 Example 193 1:2 3.40 171.6(0.272, 0.666) 420 Example 194 1-106:2-22  1:3 3.41 168.6 (0.279, 0.677)423 Example 195 1:2 3.40 170.3 (0.273, 0.678) 421 Example 1961-106:2-37  1:3 3.40 168.3 (0.273, 0.678) 420 Example 197 1:2 3.39 170.2(0.276, 0.676) 418 Example 198 1-107:2-22  1:3 3.41 169.9 (0.277, 0.668)393 Example 199 1:2 3.40 171.2 (0.277, 0.680) 391 Example 2001-108:2-24  1:3 3.41 168.2 (0.272, 0.666) 421 Example 201 1:2 3.39 170.3(0.279, 0.677) 419 Example 202 1-118:2-34  1:3 3.18 188.7 (0.277, 0.680)499 Example 202 1:2 3.16 191.9 (0.272, 0.666) 490 Example 2031-119:2-38  1:3 3.21 187.8 (0.279, 0.677) 493 Example 204 1:2 3.20 190.8(0.277, 0.668) 490 Example 205 1-141:2-45  1:3 3.40 169.7 (0.279, 0.677)422 Example 206 1:2 3.38 172.5 (0.279, 0.677) 420 Example 2071-145:2-66  1:3 3.41 168.6 (0.277, 0.680) 422 Example 208 1:2 3.40 170.5(0.272, 0.666) 421 Example 209 1-158:2-62  1:3 3.21 187.8 (0.279, 0.677)493 Example 210 1:2 3.20 190.8 (0.277, 0.668) 490 Example 2111-158:2-32  1:3 3.21 188.9 (0.277, 0.680) 501 Example 212 1:2 3.20 190.7(0.272, 0.666) 498

Looking at results of Tables 8 and 9 above, the results of Tables 8 and9 above exhibit better efficiency and lifespan effects when the compoundof Chemical Formula 1 and the compound of Chemical Formula 2 areincluded at the same time. These results may expect an exciplexphenomenon to occur when both of the compounds are included at the sametime.

The exciplex phenomenon is a phenomenon in which energy having a size ofa HOMO level of a donor (p-host) and a LUMO level of an acceptor(n-host) is emitted through electron exchange between two molecules.When a donor (p-host) with good hole transport ability and an acceptor(n-host) with good electron transport ability are used as a host of thelight emitting layer, since holes are injected into the p-host andelectrons are injected into the n-host, the driving voltage may belowered, thereby helping to improve the lifespan. In the presentdisclosure, it could be confirmed that excellent device properties areexhibited when the compound of Chemical Formula 2 above acting as adonor and the compound of Chemical Formula 1 above acting as an acceptorare used as a host for the light emitting layer.

REFERENCE NUMERAL

-   -   100: Substrate    -   200: Anode    -   300: Organic Material Layer    -   301: Hole Injection Layer    -   302: Hole Transport Layer    -   303: Light Emitting Layer    -   304: Hole Blocking Layer    -   305: Electron Transport Layer    -   306: Electron Injection Layer    -   400: Cathode

1. An organic light emitting device comprising a first electrode, asecond electrode, and an organic material layer comprising one or morelayers provided between the first electrode and the second electrode,wherein the one or more layers of the organic material layer comprise aheterocyclic compound represented by the following Chemical Formula 1and a heterocyclic compound represented by the following ChemicalFormula 2:

In Chemical Formulas 1 and 2 above, X is O; or S, R1 to R8, and Rc andRd are the same as or different from each other, and are eachindependently selected from the group including hydrogen; deuterium; ahalogen; a cyano group; a substituted or unsubstituted C1-C60 alkylgroup; a substituted or unsubstituted C2-C60 alkenyl group; asubstituted or unsubstituted C2-C60 alkynyl group; a substituted orunsubstituted C1-C60 alkoxy group; a substituted or unsubstituted C3-C60cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkylgroup; a substituted or unsubstituted C6-C60 aryl group; a substitutedor unsubstituted C2-C60 heteroaryl group; —SiRR′R″; —P(═O)RR′; and—NRR′, or two or more groups adjacent to each other are bonded to eachother to form a substituted or unsubstituted aromatic hydrocarbon ringor a substituted or unsubstituted heterocycle ring, X1 to X3 are N; orCRe, and at least one of X1 to X3 is N, L1 and L2 are the same as ordifferent from each other and are each independently a direct bond; asubstituted or unsubstituted C6-C60 arylene group; or a substituted orunsubstituted C2-C60 heteroarylene group, Ar1 and Ar2 are the same as ordifferent from each other and are each independently a substituted orunsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group,Ra and Rb are the same as or different from each other and are eachindependently —CN; —SiRR′R″; a substituted or unsubstituted C6-C60 arylgroup; or a substituted or unsubstituted C2-C60 heteroaryl group, R, R,R″, and Re are the same as or different from each other and are eachindependently hydrogen; deuterium; a substituted or unsubstituted C1-C60alkyl group; or a substituted or unsubstituted C6-C60 aryl group, n, p,and a are an integer of 0 to 4, r and s are an integer of 0 to 7, q isan integer of 1 to 5, and when n, p, a, s, q, and r are 2 or more, thesubstituents in parentheses are the same as or different from eachother.
 2. The organic light emitting device of claim 1, wherein ChemicalFormula 1 above is represented by the following Chemical Formula 3 or 4:

In Chemical Formulas 3 and 4 above, the definition of each substituentis the same as defined in Chemical Formula 1 above.
 3. The organic lightemitting device of claim 1, wherein

of Chemical Formula 1 above is represented by any one of the followingChemical Formulas 1-1 to 1-3:

In Chemical Formulas 1-1 to 1-3 above,

 means a position connected to Chemical Formula 1, and the definition ofeach substituent is the same as defined in Chemical Formula 1 above. 4.The organic light emitting device of claim 1, wherein Ar1 is representedby any one of the following Chemical Formulas 1-1-1 to 1-1-3:

In Chemical Formulas 1-1-1 to 1-1-3 above,

 means a position connected to Chemical Formula
 1. 5. The organic lightemitting device of claim 1, wherein Ar2 is represented by the followingChemical Formula 1-2-1 or 1-2-2:

In Chemical Formulas 1-2-1 and 1-2-2 above, q is the same as thedefinition in Chemical Formula 1 above,

 means a position connected to Chemical Formula 1, X1 is O; or S, R11 toR15 are the same as or different from each other, and are eachindependently selected from the group comprising hydrogen; deuterium; ahalogen; a cyano group; a substituted or unsubstituted C1-C60 alkylgroup; a substituted or unsubstituted C2-C60 alkenyl group; asubstituted or unsubstituted C2-C60 alkynyl group; a substituted orunsubstituted C1-C60 alkoxy group; a substituted or unsubstituted C3-C60cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkylgroup; a substituted or unsubstituted C6-C60 aryl group; a substitutedor unsubstituted C2-C60 heteroaryl group; —SiRR′R″; —P(═O)RR′; and—NRR′, or two or more groups adjacent to each other are bonded to eachother to form a substituted or unsubstituted aromatic hydrocarbon ringor a substituted or unsubstituted heterocycle ring, a1 is an integer of0 to 3, and when it is 2 or more, the substituents in parentheses arethe same as or different from each other, the definitions of R, R′, andR″ are the same as those in Chemical Formula 1 above, and Ar11 is asubstituted or unsubstituted C6-C60 aryl group.
 6. The organic lightemitting device of claim 1, wherein Chemical Formula 1 above isrepresented by any one of the following compounds:


7. The organic light emitting device of claim 1, wherein ChemicalFormula 2 above is represented by any one of the following compounds:


8. The organic light emitting device of claim 1, wherein the organicmaterial layer comprises at least one layer of a hole blocking layer, anelectron injection layer, and an electron transport layer, and the atleast one layer of the hole blocking layer, the electron injectionlayer, and the electron transport layer comprises a heterocycliccompound represented by Chemical Formula 1 above and a heterocycliccompound represented by Chemical Formula 2 above.
 9. The organic lightemitting device of claim 1, wherein the organic material layer comprisesa light emitting layer, and the light emitting layer comprises aheterocyclic compound represented by Chemical Formula 1 above and aheterocyclic compound represented by Chemical Formula 2 above.
 10. Theorganic light emitting device of claim 1, wherein the organic materiallayer comprises a light emitting layer, the light emitting layercomprises a host material, and the host material comprises aheterocyclic compound represented by Chemical Formula 1 above and aheterocyclic compound represented by Chemical Formula 2 above.
 11. Theorganic light emitting device of claim 1, further comprising one layeror two or more layers selected from the group comprising a lightemitting layer, a hole injection layer, a hole transport layer, anelectron injection layer, an electron transport layer, an electronblocking layer, and a hole blocking layer.
 12. A composition for theorganic material layer of the organic light emitting device, comprisingthe heterocyclic compound represented by Chemical Formula 1 above andthe heterocyclic compound represented by Chemical Formula 2 aboveaccording to claim
 1. 13. The composition for the organic material layerof the organic light emitting device of claim 12, wherein the weightratio of the heterocyclic compound represented by Chemical Formula 1above to the heterocyclic compound represented by Chemical Formula 2above in the composition is 1:10 to 10:1
 14. A method for manufacturingan organic light emitting device, comprising the steps of: preparing asubstrate; forming a first electrode on the substrate; forming anorganic material layer comprising one or more layers on the firstelectrode; and forming a second electrode on the organic material layer,wherein the step of forming the organic material layer comprises a stepof forming an organic material layer comprising one or more layers usingthe composition for the organic material layer according to claim 12.15. The method of claim 14, wherein the step of forming the organicmaterial layer is forming the organic material layer using a thermalvacuum deposition method by premixing the heterocyclic compound ofChemical Formula 1 above and the heterocyclic compound of ChemicalFormula 2 above.